209783-80-2,MFCD08272435
Catalog No.:AA002KB7

209783-80-2 | Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester

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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA002KB7
Chemical Name:
Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester
CAS Number:
209783-80-2
Molecular Formula:
C21H20N4O3
Molecular Weight:
376.4085
MDL Number:
MFCD08272435
SMILES:
O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
NSC Number:
706995
Properties
Properties
 
BP:
566.7°C at 760 mmHg  
Form:
Solid  
MP:
159-160 ºC  
Solubility:
DMSO: 38 mg/mL, soluble  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
508  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
7  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2  

Upstream Synthesis Route

[1]Patent:WO2009/76206,2009,A1,.Locationinpatent:Page/Pagecolumn16-17

[2]Patent:US6320078,2001,B1,

[3]Patent:US6320078,2001,B1,

[4]Patent:WO2017/216761,2017,A1,.Locationinpatent:Page/Pagecolumn20

[1]Patent:US6320078,2001,B1,

[1]Patent:WO2017/81278,2017,A1,.Locationinpatent:Page/Pagecolumn15

[1]ChemBioChem,2012,vol.13,#8,p.1116-1120

[1]JournalofMedicinalChemistry,1999,vol.42,#15,p.3001-3003

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

4-<N-(pyridin-3-ylmethylcarbonyl)aminomethyl>benzoylchloridehydrochloride 
  209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

Literature

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Title: HDAC1 regulates fear extinction in mice.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120411

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Journal: Brain research 20120404

Title: Selective class I histone deacetylase inhibition suppresses hypoxia-induced cardiopulmonary remodeling through an antiproliferative mechanism.

Journal: Circulation research 20120302

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Title: [Histone deacetylase inhibitor MS-275 treatment alters immune molecule content and categories in hepatocarcinoma exosomes].

Journal: Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology 20120301

Title: Histone deacetylases mediate the silencing of miR-15a, miR-16, and miR-29b in chronic lymphocytic leukemia.

Journal: Blood 20120202

Title: Histone deacetylase inhibitors enhance the anticancer activity of nutlin-3 and induce p53 hyperacetylation and downregulation of MDM2 and MDM4 gene expression.

Journal: Investigational new drugs 20120201

Title: Histone deacetylase inhibition decreases proliferation and potentiates the effect of ionizing radiation in atypical teratoid/rhabdoid tumor cells.

Journal: Neuro-oncology 20120201

Title: Phase I study of the histone deacetylase inhibitor entinostat in combination with 13-cis retinoic acid in patients with solid tumours.

Journal: British journal of cancer 20120103

Title: HDAC inhibitor MS-275 attenuates the inflammatory reaction in rat experimental autoimmune prostatitis.

Journal: The Prostate 20120101

Title: Impaired chromatin remodelling at STAT1-regulated promoters leads to global unresponsiveness of Toxoplasma gondii-infected macrophages to IFN-γ.

Journal: PLoS pathogens 20120101

Title: Class I histone deacetylase inhibitor entinostat suppresses regulatory T cells and enhances immunotherapies in renal and prostate cancer models.

Journal: PloS one 20120101

Title: Loss of deacetylation activity of Hdac6 affects emotional behavior in mice.

Journal: PloS one 20120101

Title: Histone deacetylase inhibitors globally enhance h3/h4 tail acetylation without affecting h3 lysine 56 acetylation.

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Title: Entinostat for treatment of solid tumors and hematologic malignancies.

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Title: Histone deacetylase inhibitor MS-275 stimulates bone formation in part by enhancing Dhx36-mediated TNAP transcription.

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Title: Effect of ketoconazole-mediated CYP3A4 inhibition on clinical pharmacokinetics of panobinostat (LBH589), an orally active histone deacetylase inhibitor.

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Title: Involvement of insulin-like growth factor-binding protein-3 in the effects of histone deacetylase inhibitor MS-275 in hepatoma cells.

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Journal: Urologic oncology 20100101

Title: HDAC inhibition radiosensitizes human normal tissue cells and reduces DNA Double-Strand Break repair capacity.

Journal: Oncology reports 20100101

Title: Reduced histone deacetylase 7 activity restores function to misfolded CFTR in cystic fibrosis.

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Title: Equitoxic doses of 5-azacytidine and 5-aza-2'deoxycytidine induce diverse immediate and overlapping heritable changes in the transcriptome.

Journal: PloS one 20100101

Title: New treatments for myelodysplastic syndromes.

Journal: Mediterranean journal of hematology and infectious diseases 20100101

Title: Induction of E-cadherin in lung cancer and interaction with growth suppression by histone deacetylase inhibition.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20091201

Title: Three epigenetic drugs up-regulate homeobox gene Rhox5 in cancer cells through overlapping and distinct molecular mechanisms.

Journal: Molecular pharmacology 20091101

Title: HDAC inhibitor SNDX-275 induces apoptosis in erbB2-overexpressing breast cancer cells via down-regulation of erbB3 expression.

Journal: Cancer research 20091101

Title: MDS and secondary AML display unique patterns and abundance of aberrant DNA methylation.

Journal: Blood 20091015

Title: Efficacy of MS-275, a selective inhibitor of class I histone deacetylases, in human colon cancer models.

Journal: International journal of oncology 20091001

Title: Early epigenetic changes and DNA damage do not predict clinical response in an overlapping schedule of 5-azacytidine and entinostat in patients with myeloid malignancies.

Journal: Blood 20090924

Title: HDAC inhibitors, MS275 and SBHA, enhances cytotoxicity induced by oxaliplatin in the colorectal cancer cell lines.

Journal: Biochemical and biophysical research communications 20090918

Title: Antidepressant actions of histone deacetylase inhibitors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090916

Title: Histone deacetylase inhibitors cooperate with IFN-gamma to restore caspase-8 expression and overcome TRAIL resistance in cancers with silencing of caspase-8.

Journal: Oncogene 20090903

Title: Epigenetic influences on sensory regeneration: histone deacetylases regulate supporting cell proliferation in the avian utricle.

Journal: Journal of the Association for Research in Otolaryngology : JARO 20090901

Title: Lysine acetylation targets protein complexes and co-regulates major cellular functions.

Journal: Science (New York, N.Y.) 20090814

Title: Recent advances in the development of polyamine analogues as antitumor agents.

Journal: Journal of medicinal chemistry 20090813

Title: Reactivation of death receptor 4 (DR4) expression sensitizes medulloblastoma cell lines to TRAIL.

Journal: Journal of neuro-oncology 20090701

Title: DNER, an epigenetically modulated gene, regulates glioblastoma-derived neurosphere cell differentiation and tumor propagation.

Journal: Stem cells (Dayton, Ohio) 20090701

Title: Epigenetic modifiers: basic understanding and clinical development.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090615

Title: Clinical studies of histone deacetylase inhibitors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090615

Title: Discovery of a potent class I selective ketone histone deacetylase inhibitor with antitumor activity in vivo and optimized pharmacokinetic properties.

Journal: Journal of medicinal chemistry 20090611

Title: Histone deacetylase inhibitors promote apoptosis and senescence in human mesenchymal stem cells.

Journal: Stem cells and development 20090501

Title: Epigenetic modulation of mGlu2 receptors by histone deacetylase inhibitors in the treatment of inflammatory pain.

Journal: Molecular pharmacology 20090501

Title: Inhibitors of poly ADP-ribose polymerase (PARP) induce apoptosis of myeloid leukemic cells: potential for therapy of myeloid leukemia and myelodysplastic syndromes.

Journal: Haematologica 20090501

Title: [MS-275, a histone deacetylase inhibitor, induces apoptosis and alters survivin gene expression in human myeloma cell line U266].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20090501

Title: Identification and characterization of small molecule inhibitors of a class I histone deacetylase from Plasmodium falciparum.

Journal: Journal of medicinal chemistry 20090423

Title: [Effects of histone deacetylase inhibitor MS-275 on expression of survivin and NF-kappaB in the human myeloma cell line U266 cells].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20090401

Title: Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives.

Journal: Bioorganic & medicinal chemistry 20090315

Title: Rescue of major histocompatibility-DR surface expression in retinoblastoma-defective, non-small cell lung carcinoma cells by the MS-275 histone deacetylase inhibitor.

Journal: Biological & pharmaceutical bulletin 20090301

Title: N-Benzyl-1-heteroaryl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamides as inhibitors of co-activator associated arginine methyltransferase 1 (CARM1).

Journal: Bioorganic & medicinal chemistry letters 20090215

Title: Histone acetylation resulting in resistance to methotrexate in choroid plexus cells.

Journal: Journal of neuro-oncology 20090201

Title: The reelin and GAD67 promoters are activated by epigenetic drugs that facilitate the disruption of local repressor complexes.

Journal: Molecular pharmacology 20090201

Title: Determination of a benzamide histone deacetylase inhibitor, MS-275, in human plasma by liquid chromatography with mass-spectrometric detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090115

Title: Induction of Foxp3+ regulatory T cells with histone deacetylase inhibitors.

Journal: Cellular immunology 20090101

Title: 'Shock and kill' effects of class I-selective histone deacetylase inhibitors in combination with the glutathione synthesis inhibitor buthionine sulfoximine in cell line models for HIV-1 quiescence.

Journal: Retrovirology 20090101

Title: Anti-leukemia activity of MS-275 histone deacetylase inhibitor implicates 4-1BBL/4-1BB immunomodulatory functions.

Journal: PloS one 20090101

Title: Defining the molecular action of HDAC inhibitors and synergism with androgen deprivation in ERG-positive prostate cancer.

Journal: International journal of cancer 20081215

Title: Blockade of mTOR signaling potentiates the ability of histone deacetylase inhibitor to induce growth arrest and differentiation of acute myelogenous leukemia cells.

Journal: Leukemia 20081201

Title: The histone-deacetylase inhibitor MS-275 and the CDK-inhibitor CYC-202 promote anti-tumor effects in hepatoma cell lines.

Journal: Oncology reports 20081101

Title: MS-275, a novel histone deacetylase inhibitor with selectivity against HDAC1, induces degradation of FLT3 via inhibition of chaperone function of heat shock protein 90 in AML cells.

Journal: Leukemia research 20080901

Title: Pharmacodynamic assessment of histone deacetylase inhibitors: infrared vibrational spectroscopic imaging of protein acetylation.

Journal: Analytical chemistry 20080815

Title: Sp1-mediated TRAIL induction in chemosensitization.

Journal: Cancer research 20080815

Title: Multicenter phase II trial of the histone deacetylase inhibitor pyridylmethyl-N-{4-[(2-aminophenyl)-carbamoyl]-benzyl}-carbamate in pretreated metastatic melanoma.

Journal: Melanoma research 20080801

Title: A phase I and pharmacokinetic study of the oral histone deacetylase inhibitor, MS-275, in patients with refractory solid tumors and lymphomas.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080715

Title: Inhibition of MEK/ERK signaling synergistically potentiates histone deacetylase inhibitor-induced growth arrest, apoptosis and acetylation of histone H3 on p21waf1 promoter in acute myelogenous leukemia cell.

Journal: Leukemia 20080701

Title: p21(WAF1/CIP1) induction by 5-azacytosine nucleosides requires DNA damage.

Journal: Oncogene 20080605

Title: Histone deacetylase inhibitors induce growth arrest, apoptosis, and differentiation in clear cell sarcoma models.

Journal: Molecular cancer therapeutics 20080601

Title: Evaluation of the in vitro and in vivo antitumor activity of histone deacetylase inhibitors for the therapy of retinoblastoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080515

Title: Potentiation of reactive oxygen species is a marker for synergistic cytotoxicity of MS-275 and 5-azacytidine in leukemic cells.

Journal: Leukemia research 20080501

Title: Novel uracil-based 2-aminoanilide and 2-aminoanilide-like derivatives: histone deacetylase inhibition and in-cell activities.

Journal: Bioorganic & medicinal chemistry letters 20080415

Title: MS-275 synergistically enhances the growth inhibitory effects of RAMBA VN/66-1 in hormone-insensitive PC-3 prostate cancer cells and tumours.

Journal: British journal of cancer 20080408

Title: Identification of ligand features essential for HDACs inhibitors by pharmacophore modeling.

Journal: Journal of molecular graphics & modelling 20080401

Title: Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts.

Journal: Bioorganic & medicinal chemistry 20080315

Title: Probing the elusive catalytic activity of vertebrate class IIa histone deacetylases.

Journal: Bioorganic & medicinal chemistry letters 20080315

Title: Acute-myeloid-leukemia-targeted toxins kill tumor cells by cell-type-specific mechanisms and synergize with TRAIL to allow manipulation of the extent and mechanism of tumor cell death.

Journal: Leukemia 20080301

Title: Histone deacetylase inhibitors in lymphoma and solid malignancies.

Journal: Expert review of anticancer therapy 20080301

Title: Regulation of arginase-1 expression in macrophages by a protein kinase A type I and histone deacetylase dependent pathway.

Journal: Journal of cellular biochemistry 20080201

Title: Histone deacetylase inhibitors induce growth arrest and apoptosis of HTLV-1-infected T-cells via blockade of signaling by nuclear factor kappaB.

Journal: Leukemia research 20080201

Title: Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors.

Journal: The Biochemical journal 20080115

Title: Antiproliferative activities of a library of hybrids between indanones and HDAC inhibitor SAHA and MS-275 analogues.

Journal: Bioorganic & medicinal chemistry letters 20071115

Title: Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity.

Journal: Journal of medicinal chemistry 20071115

Title: Histone deacetylase inhibitors induce cell death and enhance the apoptosis-inducing activity of TRAIL in Ewing's sarcoma cells.

Journal: Journal of cancer research and clinical oncology 20071101

Title: Histone deacetylase inhibitors suppress TF-kappaB-dependent agonist-driven tissue factor expression in endothelial cells and monocytes.

Journal: The Journal of biological chemistry 20070928

Title: Phase I trial of MS-275, a histone deacetylase inhibitor, administered weekly in refractory solid tumors and lymphoid malignancies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070915

Title: Histone deacetylase inhibitor MS-275 alone or combined with bortezomib or sorafenib exhibits strong antiproliferative action in human cholangiocarcinoma cells.

Journal: World journal of gastroenterology 20070907

Title: Trithiocarbonates: exploration of a new head group for HDAC inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20070901

Title: Relationship between embryonic histonic hyperacetylation and axial skeletal defects in mouse exposed to the three HDAC inhibitors apicidin, MS-275, and sodium butyrate.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070801

Title: Antitumor activity of the histone deacetylase inhibitor MS-275 in prostate cancer models.

Journal: The Prostate 20070801

Title: Synergistic in vivo antitumor effect of the histone deacetylase inhibitor MS-275 in combination with interleukin 2 in a murine model of renal cell carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070801

Title: Histone deacetylase inhibitors affect dendritic cell differentiation and immunogenicity.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070701

Title: Bispyridinium dienes: histone deacetylase inhibitors with selective activities.

Journal: Journal of medicinal chemistry 20070517

Title: MAGE-A9 mRNA and protein expression in bladder cancer.

Journal: International journal of cancer 20070515

Title: Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid.

Journal: Bioorganic & medicinal chemistry letters 20070415

Title: Phase 1 and pharmacologic study of MS-275, a histone deacetylase inhibitor, in adults with refractory and relapsed acute leukemias.

Journal: Blood 20070401

Title: Anti-rheumatic activities of histone deacetylase (HDAC) inhibitors in vivo in collagen-induced arthritis in rodents.

Journal: British journal of pharmacology 20070401

Title: The histone deacetylase inhibitors depsipeptide and MS-275, enhance TRAIL gene therapy of LNCaP prostate cancer cells without adverse effects in normal prostate epithelial cells.

Journal: Cancer gene therapy 20070301

Title: A liquid chromatography/tandem mass spectrometry assay to quantitate MS-275 in human plasma.

Journal: Journal of pharmaceutical and biomedical analysis 20070117

Title: Measuring cytotoxicity: a new perspective on LC50.

Journal: Anticancer research 20070101

Title: MS-275, a potent orally available inhibitor of histone deacetylases--the development of an anticancer agent.

Journal: The international journal of biochemistry & cell biology 20070101

Title: HDAC inhibitors induce apoptosis in glucocorticoid-resistant acute lymphatic leukemia cells despite a switch from the extrinsic to the intrinsic death pathway.

Journal: The international journal of biochemistry & cell biology 20070101

Title: Antiproliferative and proapoptotic effects of histone deacetylase inhibitors on gastrointestinal neuroendocrine tumor cells.

Journal: Endocrine-related cancer 20061201

Title: Factors affecting the pharmacokinetic profile of MS-275, a novel histone deacetylase inhibitor, in patients with cancer.

Journal: Investigational new drugs 20060901

Title: Substituted N-(2-aminophenyl)-benzamides, (E)-N-(2-aminophenyl)-acrylamides and their analogues: novel classes of histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20060801

Title: Ex vivo therapy of malignant melanomas transplanted into organotypic brain slice cultures using inhibitors of histone deacetylases.

Journal: Acta neuropathologica 20060801

Title: Experimental therapy of malignant gliomas using the inhibitor of histone deacetylase MS-275.

Journal: Molecular cancer therapeutics 20060501

Title: Curcumin is an inhibitor of p300 histone acetylatransferase.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20060301

Title: Interspecies differences in plasma protein binding of MS-275, a novel histone deacetylase inhibitor.

Journal: Cancer chemotherapy and pharmacology 20060201

Title: Anticancer activity of MS-275, a novel histone deacetylase inhibitor, against human endometrial cancer cells.

Journal: Anticancer research 20060101

Title: Bombesin/gastrin-releasing peptide receptor antagonists increase the ability of histone deacetylase inhibitors to reduce lung cancer proliferation.

Journal: Journal of molecular neuroscience : MN 20060101

Title: Histone deacetylase inhibitors in cancer therapy.

Journal: Cancer investigation 20060101

Title: Histone deacetylase inhibitors promote osteoblast maturation.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20051201

Title: Targeting epigenetic changes in acute myeloid leukemia.

Journal: Clinical advances in hematology & oncology : H&O 20051101

Title: Early clinical data and potential clinical utility of novel histone deacetylase inhibitors in prostate cancer.

Journal: Clinical prostate cancer 20050901

Title: Blockade of histone deacetylase inhibitor-induced RelA/p65 acetylation and NF-kappaB activation potentiates apoptosis in leukemia cells through a process mediated by oxidative damage, XIAP downregulation, and c-Jun N-terminal kinase 1 activation.

Journal: Molecular and cellular biology 20050701

Title: [A new target of cancer therapy: advances in the study of histone deacetylase].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20050701

Title: In vivo imaging of retinoic acid receptor beta2 transcriptional activation by the histone deacetylase inhibitor MS-275 in retinoid-resistant prostate cancer cells.

Journal: The Prostate 20050615

Title: Phase I and pharmacokinetic study of MS-275, a histone deacetylase inhibitor, in patients with advanced and refractory solid tumors or lymphoma.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050610

Title: Epigenetic modulation of retinoic acid receptor beta2 by the histone deacetylase inhibitor MS-275 in human renal cell carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050501

Title: Histone deacetylase inhibitors and cancer: from cell biology to the clinic.

Journal: European journal of cell biology 20050301

Title: Peak shape improvement of basic analytes in capillary liquid chromatography.

Journal: Journal of separation science 20050201

Title: Histone deacetylase inhibitor pharmacodynamic analysis by multiparameter flow cytometry.

Journal: Annals of clinical and laboratory science 20050101

Title: Enhancement of xenograft tumor radiosensitivity by the histone deacetylase inhibitor MS-275 and correlation with histone hyperacetylation.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040915

Title: Histone deacetylase inhibitor enhances the anti-leukemic activity of an established nucleoside analogue.

Journal: Cancer biology & therapy 20040801

Title: The histone deacetylase inhibitor MS-275 induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia cells.

Journal: Leukemia 20040701

Title: Histone deacetylase inhibitors FK228, N-(2-aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl)amino- methyl]benzamide and m-carboxycinnamic acid bis-hydroxamide augment radiation-induced cell death in gastrointestinal adenocarcinoma cells.

Journal: International journal of cancer 20040610

Title: Determination of MS-275, a novel histone deacetylase inhibitor, in human plasma by liquid chromatography-electrospray mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040525

Title: The histone deacetylase inhibitor MS-275 interacts synergistically with fludarabine to induce apoptosis in human leukemia cells.

Journal: Cancer research 20040401

Title: (2-amino-phenyl)-amides of omega-substituted alkanoic acids as new histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20040105

Title: Enhanced radiation-induced cell killing and prolongation of gammaH2AX foci expression by the histone deacetylase inhibitor MS-275.

Journal: Cancer research 20040101

Title: Synthesis and biological evaluation of 3-(4-substituted-phenyl)-N-hydroxy-2-propenamides, a new class of histone deacetylase inhibitors.

Journal: Journal of medicinal chemistry 20031218

Title: Identification of novel isoform-selective inhibitors within class I histone deacetylases.

Journal: The Journal of pharmacology and experimental therapeutics 20031101

Title: Inhibition of PI-3 kinase sensitizes human leukemic cells to histone deacetylase inhibitor-mediated apoptosis through p44/42 MAP kinase inactivation and abrogation of p21(CIP1/WAF1) induction rather than AKT inhibition.

Journal: Oncogene 20030918

Title: The histone deacetylase inhibitor MS-275 promotes differentiation or apoptosis in human leukemia cells through a process regulated by generation of reactive oxygen species and induction of p21CIP1/WAF1 1.

Journal: Cancer research 20030701

Title: Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin.

Journal: Blood 20030301

Title: Gene expression profiling of multiple histone deacetylase (HDAC) inhibitors: defining a common gene set produced by HDAC inhibition in T24 and MDA carcinoma cell lines.

Journal: Molecular cancer therapeutics 20030201

Title: Trifluoromethyl ketones as inhibitors of histone deacetylase.

Journal: Bioorganic & medicinal chemistry letters 20021202

Title: MS-27-275, an inhibitor of histone deacetylase, has marked in vitro and in vivo antitumor activity against pediatric solid tumors.

Journal: Cancer research 20021101

Title: Sulfonamide anilides, a novel class of histone deacetylase inhibitors, are antiproliferative against human tumors.

Journal: Cancer research 20020801

Title: Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group.

Journal: Bioorganic & medicinal chemistry letters 20020520

Title: Transcriptional regulation of the transforming growth factor beta type II receptor gene by histone acetyltransferase and deacetylase is mediated by NF-Y in human breast cancer cells.

Journal: The Journal of biological chemistry 20020215

Title: MS-275, a histone deacetylase inhibitor, selectively induces transforming growth factor beta type II receptor expression in human breast cancer cells.

Journal: Cancer research 20010201

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Title: Saito A, et al. A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors. Proc Natl Acad Sci U S A, 1999, 96(8), 4592-4597.

Title: Zhang ZY, et al. MS-275, an histone deacetylase inhibitor, reduces the inflammatory reaction in rat experimental autoimmune neuritis. Neurosci, 2010, 169, 370-377.

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Tags:209783-80-2 Molecular Formula|209783-80-2 MDL|209783-80-2 SMILES|209783-80-2 Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester
Catalog No.: AA002KB7
209783-80-2,MFCD08272435
209783-80-2 | Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester
Pack Size: 1mg
Purity: 98%
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Technical Information
Catalog Number: AA002KB7
Chemical Name: Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester
CAS Number: 209783-80-2
Molecular Formula: C21H20N4O3
Molecular Weight: 376.4085
MDL Number: MFCD08272435
SMILES: O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
NSC Number: 706995
Properties
BP: 566.7°C at 760 mmHg  
Form: Solid  
MP: 159-160 ºC  
Solubility: DMSO: 38 mg/mL, soluble  
Storage: Keep in dry area;-20 ℃;  
Complexity: 508  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 28  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 7  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2  
Upstream Synthesis Route
95-54-5    241809-79-0    209783-80-2 

[1]Patent:WO2009/76206,2009,A1,.Locationinpatent:Page/Pagecolumn16-17

[2]Patent:US6320078,2001,B1,

[3]Patent:US6320078,2001,B1,

[4]Patent:WO2017/216761,2017,A1,.Locationinpatent:Page/Pagecolumn20

80-73-9    95-54-5    241809-79-0    209783-80-2 

[1]Patent:US6320078,2001,B1,

95-54-5    530-62-1    241809-79-0    209783-80-2 

[1]Patent:WO2017/81278,2017,A1,.Locationinpatent:Page/Pagecolumn15

1379471-51-8    209783-80-2 

[1]ChemBioChem,2012,vol.13,#8,p.1116-1120

100-55-0    209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,#15,p.3001-3003

Downstream Synthesis Route
95-54-5    255894-58-7    209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

100-55-0    209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

212632-27-4    209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

241809-79-0    209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

4-<N-(pyridin-3-ylmethylcarbonyl)aminomethyl>benzoylchloridehydrochloride 
  209783-80-2 

[1]JournalofMedicinalChemistry,1999,vol.42,p.3001-3003

Literature fold

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Journal: Archives of toxicology20180701

Title: A precision oncology approach to the pharmacological targeting of mechanistic dependencies in neuroendocrine tumors.

Journal: Nature genetics20180701

Title: Fingerprinting of neurotoxic compounds using a mouse embryonic stem cell dual luminescence reporter assay.

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Title: Definition of transcriptome-based indices for quantitative characterization of chemically disturbed stem cell development: introduction of the STOP-Tox(ukn) and STOP-Tox(ukk) tests.

Journal: Archives of toxicology20170101

Title: Histone deacetylase inhibitors decrease NHEJ both by acetylation of repair factors and trapping of PARP1 at DNA double-strand breaks in chromatin.

Journal: Leukemia research20160601

Title: Epigenetic Modulators and the New Immunotherapies.

Journal: The New England journal of medicine20160218

Title: The Effects of Class-Specific Histone Deacetylase Inhibitors on the Development of Limbs During Organogenesis.

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Title: Deacetylase inhibitors repress STAT5-mediated transcription by interfering with bromodomain and extra-terminal (BET) protein function.

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Title: Identification of histone deacetylase inhibitors with benzoylhydrazide scaffold that selectively inhibit class I histone deacetylases.

Journal: Chemistry & biology20150219

Title: A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors.

Journal: Archives of toxicology20150101

Title: Histone deacetylase 4 promotes ubiquitin-dependent proteasomal degradation of Sp3 in SH-SY5Y cells treated with di(2-ethylhexyl)phthalate (DEHP), determining neuronal death.

Journal: Toxicology and applied pharmacology20141001

Title: Histone deacetylase inhibitor valproic acid promotes the differentiation of human induced pluripotent stem cells into hepatocyte-like cells.

Journal: PloS one20140101

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters20130801

Title: The structural requirements of histone deacetylase inhibitors: suberoylanilide hydroxamic acid analogs modified at the C6 position.

Journal: Bioorganic & medicinal chemistry letters20121201

Title: A combined approach for the study of histone deacetylase inhibitors.

Journal: Molecular bioSystems20121101

Title: Histone deacetylase inhibitors preserve function in aging axons.

Journal: Journal of neurochemistry20121101

Title: Novel agents in Hodgkin lymphoma.

Journal: Current oncology reports20121001

Title: P300/CBP associated factor regulates nitroglycerin-dependent arterial relaxation by N(ε)-lysine acetylation of contractile proteins.

Journal: Arteriosclerosis, thrombosis, and vascular biology20121001

Title: MS-275, a benzamide histone deacetylase inhibitor, prevents osteoclastogenesis by down-regulating c-Fos expression and suppresses bone loss in mice.

Journal: European journal of pharmacology20120915

Title: Effect of valproic acid on mitochondrial epigenetics.

Journal: European journal of pharmacology20120905

Title: HDAC2 regulates atypical antipsychotic responses through the modulation of mGlu2 promoter activity.

Journal: Nature neuroscience20120901

Title: Histone deacetylase inhibitors: structure-based modeling and isoform-selectivity prediction.

Journal: Journal of chemical information and modeling20120827

Title: P38 MAP kinase functions as a switch in MS-275-induced reactive oxygen species-dependent autophagy and apoptosis in human colon cancer cells.

Journal: Free radical biology & medicine20120801

Title: Synthesis, biological evaluation and molecular docking studies of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives as inhibitors of HDAC activity.

Journal: Bioorganic & medicinal chemistry20120715

Title: Increased neuron specific enolase expression by urothelial cells exposed to or malignantly transformed by exposure to Cd²⁺ or As³⁺.

Journal: Toxicology letters20120707

Title: Trichostatin A induces 5-lipoxygenase promoter activity and mRNA expression via inhibition of histone deacetylase 2 and 3.

Journal: Journal of cellular and molecular medicine20120701

Title: Appraisal of GABA and PABA as linker: design and synthesis of novel benzamide based histone deacetylase inhibitors.

Journal: European journal of medicinal chemistry20120701

Title: Histone deacetylase inhibition modulates E-cadherin expression and suppresses migration and invasion of anaplastic thyroid cancer cells.

Journal: The Journal of clinical endocrinology and metabolism20120701

Title: Inhibition of histone deacetylase 3 protects beta cells from cytokine-induced apoptosis.

Journal: Chemistry & biology20120622

Title: Randomized phase II trial of erlotinib with and without entinostat in patients with advanced non-small-cell lung cancer who progressed on prior chemotherapy.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20120620

Title: Antitumor activity of Chidamide in hepatocellular carcinoma cell lines.

Journal: Molecular medicine reports20120601

Title: HDAC1 regulates fear extinction in mice.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20120411

Title: Molecular mechanisms associated with the antidepressant effects of the class I histone deacetylase inhibitor MS-275 in the rat ventrolateral orbital cortex.

Journal: Brain research20120404

Title: Selective class I histone deacetylase inhibition suppresses hypoxia-induced cardiopulmonary remodeling through an antiproliferative mechanism.

Journal: Circulation research20120302

Title: Anti-tumor activity of new orally bioavailable 2-amino-5-(thiophen-2-yl)benzamide-series histone deacetylase inhibitors, possessing an aqueous soluble functional group as a surface recognition domain.

Journal: Bioorganic & medicinal chemistry letters20120301

Title: [Histone deacetylase inhibitor MS-275 treatment alters immune molecule content and categories in hepatocarcinoma exosomes].

Journal: Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology20120301

Title: Histone deacetylases mediate the silencing of miR-15a, miR-16, and miR-29b in chronic lymphocytic leukemia.

Journal: Blood20120202

Title: Histone deacetylase inhibitors enhance the anticancer activity of nutlin-3 and induce p53 hyperacetylation and downregulation of MDM2 and MDM4 gene expression.

Journal: Investigational new drugs20120201

Title: Histone deacetylase inhibition decreases proliferation and potentiates the effect of ionizing radiation in atypical teratoid/rhabdoid tumor cells.

Journal: Neuro-oncology20120201

Title: Phase I study of the histone deacetylase inhibitor entinostat in combination with 13-cis retinoic acid in patients with solid tumours.

Journal: British journal of cancer20120103

Title: HDAC inhibitor MS-275 attenuates the inflammatory reaction in rat experimental autoimmune prostatitis.

Journal: The Prostate20120101

Title: Impaired chromatin remodelling at STAT1-regulated promoters leads to global unresponsiveness of Toxoplasma gondii-infected macrophages to IFN-γ.

Journal: PLoS pathogens20120101

Title: Class I histone deacetylase inhibitor entinostat suppresses regulatory T cells and enhances immunotherapies in renal and prostate cancer models.

Journal: PloS one20120101

Title: Loss of deacetylation activity of Hdac6 affects emotional behavior in mice.

Journal: PloS one20120101

Title: Histone deacetylase inhibitors globally enhance h3/h4 tail acetylation without affecting h3 lysine 56 acetylation.

Journal: Scientific reports20120101

Title: Differential epigenetic regulation of TOX subfamily high mobility group box genes in lung and breast cancers.

Journal: PloS one20120101

Title: Novel therapies for aggressive B-cell lymphoma.

Journal: Advances in hematology20120101

Title: Vorinostat approved in Japan for treatment of cutaneous T-cell lymphomas: status and prospects.

Journal: OncoTargets and therapy20120101

Title: A heterodimeric glucuronide prodrug for cancer tritherapy: the double role of the chemical amplifier.

Journal: ChemMedChem20111209

Title: Inhibitors of histone deacetylases in class I and class II suppress human osteoclasts in vitro.

Journal: Journal of cellular physiology20111201

Title: Histone deacetylase inhibitors and periodontal bone loss.

Journal: Journal of periodontal research20111201

Title: Raman microspectroscopy detects epigenetic modifications in living Jurkat leukemic cells.

Journal: Epigenomics20111201

Title: Combination epigenetic therapy has efficacy in patients with refractory advanced non-small cell lung cancer.

Journal: Cancer discovery20111201

Title: The structural requirements of histone deacetylase inhibitors: Suberoylanilide hydroxamic acid analogs modified at the C3 position display isoform selectivity.

Journal: Bioorganic & medicinal chemistry letters20111015

Title: The histone deacetylase inhibitor entinostat (SNDX-275) induces apoptosis in Hodgkin lymphoma cells and synergizes with Bcl-2 family inhibitors.

Journal: Experimental hematology20111001

Title: Entinostat for treatment of solid tumors and hematologic malignancies.

Journal: Expert opinion on investigational drugs20111001

Title: Histone deacetylase inhibitor MS-275 stimulates bone formation in part by enhancing Dhx36-mediated TNAP transcription.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research20110901

Title: Effect of ketoconazole-mediated CYP3A4 inhibition on clinical pharmacokinetics of panobinostat (LBH589), an orally active histone deacetylase inhibitor.

Journal: Cancer chemotherapy and pharmacology20110901

Title: Involvement of insulin-like growth factor-binding protein-3 in the effects of histone deacetylase inhibitor MS-275 in hepatoma cells.

Journal: The Journal of biological chemistry20110826

Title: Combined inhibitors of angiogenesis and histone deacetylase: efficacy in rat hepatoma.

Journal: World journal of gastroenterology20110821

Title: Design, synthesis and docking studies on benzamide derivatives as histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters20110815

Title: Effect of the histone deacetylase inhibitor SNDX-275 on Fas signaling in osteosarcoma cells and the feasibility of its topical application for the treatment of osteosarcoma lung metastases.

Journal: Cancer20110801

Title: HDAC inhibitor SNDX-275 enhances efficacy of trastuzumab in erbB2-overexpressing breast cancer cells and exhibits potential to overcome trastuzumab resistance.

Journal: Cancer letters20110801

Title: Schizophrenia is associated with dysregulation of a Cdk5 activator that regulates synaptic protein expression and cognition.

Journal: Brain : a journal of neurology20110801

Title: A novel HDAC inhibitor with a hydroxy-pyrimidine scaffold.

Journal: Bioorganic & medicinal chemistry letters20110715

Title: Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors.

Journal: Journal of medicinal chemistry20110714

Title: The HDAC class I-specific inhibitor entinostat (MS-275) effectively relieves epigenetic silencing of the LAT2 gene mediated by AML1/ETO.

Journal: Oncogene20110707

Title: Aromatase inhibitors and xenograft studies.

Journal: Steroids20110701

Title: Simultaneous inhibition of DNA methyltransferase and histone deacetylase induces p53-independent apoptosis via down-regulation of Mcl-1 in acute myelogenous leukemia cells.

Journal: Leukemia research20110701

Title: Chemosensitization of glioblastoma cells by the histone deacetylase inhibitor MS275.

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Title: Epigenetic profiling of the antitumor natural product psammaplin A and its analogues.

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Title: Analysis of the GAD1 promoter: trans-acting factors and DNA methylation converge on the 5' untranslated region.

Journal: Neuropharmacology20110601

Title: Histone deacetylase inhibition alters histone methylation associated with heat shock protein 70 promoter modifications in astrocytes and neurons.

Journal: Neuropharmacology20110601

Title: Post-training intrahippocampal inhibition of class I histone deacetylases enhances long-term object-location memory.

Journal: Learning & memory (Cold Spring Harbor, N.Y.)20110601

Title: Clinical development of panobinostat in classical Hodgkin's lymphoma.

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Title: HDAC inhibitors potentiate the activity of the BCR/ABL kinase inhibitor KW-2449 in imatinib-sensitive or -resistant BCR/ABL+ leukemia cells in vitro and in vivo.

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Title: Hippocampal-dependent antidepressant-like activity of histone deacetylase inhibition.

Journal: Neuroscience letters20110415

Title: Functional activation of the estrogen receptor-α and aromatase by the HDAC inhibitor entinostat sensitizes ER-negative tumors to letrozole.

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Title: [Design, synthesis, and biological activities of histone deacetylase inhibitors with diketo ester as zinc binding group].

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Title: Deacetylation of the DNA-binding domain regulates p53-mediated apoptosis.

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Title: DNA methylation changes following 5-azacitidine treatment in patients with myelodysplastic syndrome.

Journal: Journal of Korean medical science20110201

Title: Combination therapy with vidaza and entinostat suppresses tumor growth and reprograms the epigenome in an orthotopic lung cancer model.

Journal: Cancer research20110115

Title: Histone deacetylase inhibitors stimulate histone H3 lysine 4 methylation in part via transcriptional repression of histone H3 lysine 4 demethylases.

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Title: Application of p21 and klf2 reporter gene assays to identify selective histone deacetylase inhibitors for cancer therapy.

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Title: Histone deacetylase inhibitors in the treatment of hematological malignancies and solid tumors.

Journal: Journal of biomedicine & biotechnology20110101

Title: Manipulating protein acetylation in breast cancer: a promising approach in combination with hormonal therapies?

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Title: Differences in the epigenetic regulation of MT-3 gene expression between parental and Cd+2 or As+3 transformed human urothelial cells.

Journal: Cancer cell international20110101

Title: Homeobox gene Rhox5 is regulated by epigenetic mechanisms in cancer and stem cells and promotes cancer growth.

Journal: Molecular cancer20110101

Title: Enhancer of zeste homolog 2 (EZH2) in pediatric soft tissue sarcomas: first implications.

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Title: Interpreting clinical assays for histone deacetylase inhibitors.

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Title: Myelodysplastic syndrome and histone deacetylase inhibitors: 'to be or not to be acetylated'?

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Title: Therapeutic strategies to enhance the anticancer efficacy of histone deacetylase inhibitors.

Journal: Journal of biomedicine & biotechnology20110101

Title: Epigenetics in breast cancer: what's new?

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Title: Epigenetics in prostate cancer.

Journal: Prostate cancer20110101

Title: Romidepsin in the treatment of cutaneous T-cell lymphoma.

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Title: Therapy of thyroid carcinoma with the histone deacetylase inhibitor MS-275.

Journal: European journal of nuclear medicine and molecular imaging20101201

Title: Inhibitors selective for HDAC6 in enzymes and cells.

Journal: Bioorganic & medicinal chemistry letters20101201

Title: MS-275 sensitizes TRAIL-resistant breast cancer cells, inhibits angiogenesis and metastasis, and reverses epithelial-mesenchymal transition in vivo.

Journal: Molecular cancer therapeutics20101201

Title: The DAC system and associations with multiple myeloma.

Journal: Investigational new drugs20101201

Title: Histone deacetylase inhibitors in Hodgkin lymphoma.

Journal: Investigational new drugs20101201

Title: Histone deacetylase inhibitors: potential targets responsible for their anti-cancer effect.

Journal: Investigational new drugs20101201

Title: Impact of histone deacetylase inhibitors SAHA and MS-275 on DNA repair pathways in human mesenchymal stem cells.

Journal: Journal of cellular physiology20101101

Title: Autophagy potentiates the anti-cancer effects of the histone deacetylase inhibitors in hepatocellular carcinoma.

Journal: Autophagy20101101

Title: Histone deacetylase inhibitors in the treatment of lymphoma.

Journal: Discovery medicine20101101

Title: Absence of Metallothionein 3 Expression in Breast Cancer is a Rare, But Favorable Marker of Outcome that is Under Epigenetic Control.

Journal: Toxicological and environmental chemistry20101001

Title: Histone deacetylase inhibitors in lymphoma.

Journal: Current opinion in oncology20100901

Title: MS-275, an histone deacetylase inhibitor, reduces the inflammatory reaction in rat experimental autoimmune neuritis.

Journal: Neuroscience20100811

Title: Histone deacetylase inhibitors MS-275 and SAHA induced growth arrest and suppressed lipopolysaccharide-stimulated NF-kappaB p65 nuclear accumulation in human rheumatoid arthritis synovial fibroblastic E11 cells.

Journal: Rheumatology (Oxford, England)20100801

Title: American Society of Clinical Oncology--46th annual meeting.

Journal: IDrugs : the investigational drugs journal20100801

Title: Synthesis and biological characterization of the histone deacetylase inhibitor largazole and C7- modified analogues.

Journal: Journal of medicinal chemistry20100624

Title: New orally bioavailable 2-aminobenzamide-type histone deacetylase inhibitor possessing a (2-hydroxyethyl)(4-(thiophen-2-yl)benzyl)amino group.

Journal: Bioorganic & medicinal chemistry20100601

Title: Epigenetic therapy of lymphoma using histone deacetylase inhibitors.

Journal: Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico20100601

Title: [Histone acetylation, gene regulation and depression].

Journal: Medecine sciences : M/S20100501

Title: Chemical phylogenetics of histone deacetylases.

Journal: Nature chemical biology20100301

Title: MS275 enhances cytotoxicity induced by 5-fluorouracil in the colorectal cancer cells.

Journal: European journal of pharmacology20100210

Title: Induction of TAp63 by histone deacetylase inhibitors.

Journal: Biochemical and biophysical research communications20100122

Title: Histone deacetylase inhibitors induce thyroid cancer-specific apoptosis through proteasome-dependent inhibition of TRAIL degradation.

Journal: Oncogene20100107

Title: Experimental study on inhibitory effects of histone deacetylase inhibitor MS-275 and TSA on bladder cancer cells.

Journal: Urologic oncology20100101

Title: HDAC inhibition radiosensitizes human normal tissue cells and reduces DNA Double-Strand Break repair capacity.

Journal: Oncology reports20100101

Title: Reduced histone deacetylase 7 activity restores function to misfolded CFTR in cystic fibrosis.

Journal: Nature chemical biology20100101

Title: Histone deacetylase inhibitors induce apoptosis in human eosinophils and neutrophils.

Journal: Journal of inflammation (London, England)20100101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20100101

Title: The novel deacetylase inhibitor AR-42 demonstrates pre-clinical activity in B-cell malignancies in vitro and in vivo.

Journal: PloS one20100101

Title: An update on the safety and efficacy of decitabine in the treatment of myelodysplastic syndromes.

Journal: OncoTargets and therapy20100101

Title: Epigenetic approaches in the treatment of myelodysplastic syndromes: clinical utility of azacitidine.

Journal: OncoTargets and therapy20100101

Title: Equitoxic doses of 5-azacytidine and 5-aza-2'deoxycytidine induce diverse immediate and overlapping heritable changes in the transcriptome.

Journal: PloS one20100101

Title: New treatments for myelodysplastic syndromes.

Journal: Mediterranean journal of hematology and infectious diseases20100101

Title: Induction of E-cadherin in lung cancer and interaction with growth suppression by histone deacetylase inhibition.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer20091201

Title: Three epigenetic drugs up-regulate homeobox gene Rhox5 in cancer cells through overlapping and distinct molecular mechanisms.

Journal: Molecular pharmacology20091101

Title: HDAC inhibitor SNDX-275 induces apoptosis in erbB2-overexpressing breast cancer cells via down-regulation of erbB3 expression.

Journal: Cancer research20091101

Title: MDS and secondary AML display unique patterns and abundance of aberrant DNA methylation.

Journal: Blood20091015

Title: Efficacy of MS-275, a selective inhibitor of class I histone deacetylases, in human colon cancer models.

Journal: International journal of oncology20091001

Title: Early epigenetic changes and DNA damage do not predict clinical response in an overlapping schedule of 5-azacytidine and entinostat in patients with myeloid malignancies.

Journal: Blood20090924

Title: HDAC inhibitors, MS275 and SBHA, enhances cytotoxicity induced by oxaliplatin in the colorectal cancer cell lines.

Journal: Biochemical and biophysical research communications20090918

Title: Antidepressant actions of histone deacetylase inhibitors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20090916

Title: Histone deacetylase inhibitors cooperate with IFN-gamma to restore caspase-8 expression and overcome TRAIL resistance in cancers with silencing of caspase-8.

Journal: Oncogene20090903

Title: Epigenetic influences on sensory regeneration: histone deacetylases regulate supporting cell proliferation in the avian utricle.

Journal: Journal of the Association for Research in Otolaryngology : JARO20090901

Title: Lysine acetylation targets protein complexes and co-regulates major cellular functions.

Journal: Science (New York, N.Y.)20090814

Title: Recent advances in the development of polyamine analogues as antitumor agents.

Journal: Journal of medicinal chemistry20090813

Title: Reactivation of death receptor 4 (DR4) expression sensitizes medulloblastoma cell lines to TRAIL.

Journal: Journal of neuro-oncology20090701

Title: DNER, an epigenetically modulated gene, regulates glioblastoma-derived neurosphere cell differentiation and tumor propagation.

Journal: Stem cells (Dayton, Ohio)20090701

Title: Epigenetic modifiers: basic understanding and clinical development.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20090615

Title: Clinical studies of histone deacetylase inhibitors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20090615

Title: Discovery of a potent class I selective ketone histone deacetylase inhibitor with antitumor activity in vivo and optimized pharmacokinetic properties.

Journal: Journal of medicinal chemistry20090611

Title: Histone deacetylase inhibitors promote apoptosis and senescence in human mesenchymal stem cells.

Journal: Stem cells and development20090501

Title: Epigenetic modulation of mGlu2 receptors by histone deacetylase inhibitors in the treatment of inflammatory pain.

Journal: Molecular pharmacology20090501

Title: Inhibitors of poly ADP-ribose polymerase (PARP) induce apoptosis of myeloid leukemic cells: potential for therapy of myeloid leukemia and myelodysplastic syndromes.

Journal: Haematologica20090501

Title: [MS-275, a histone deacetylase inhibitor, induces apoptosis and alters survivin gene expression in human myeloma cell line U266].

Journal: Ai zheng = Aizheng = Chinese journal of cancer20090501

Title: Identification and characterization of small molecule inhibitors of a class I histone deacetylase from Plasmodium falciparum.

Journal: Journal of medicinal chemistry20090423

Title: [Effects of histone deacetylase inhibitor MS-275 on expression of survivin and NF-kappaB in the human myeloma cell line U266 cells].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology]20090401

Title: Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives.

Journal: Bioorganic & medicinal chemistry20090315

Title: Rescue of major histocompatibility-DR surface expression in retinoblastoma-defective, non-small cell lung carcinoma cells by the MS-275 histone deacetylase inhibitor.

Journal: Biological & pharmaceutical bulletin20090301

Title: N-Benzyl-1-heteroaryl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamides as inhibitors of co-activator associated arginine methyltransferase 1 (CARM1).

Journal: Bioorganic & medicinal chemistry letters20090215

Title: Histone acetylation resulting in resistance to methotrexate in choroid plexus cells.

Journal: Journal of neuro-oncology20090201

Title: The reelin and GAD67 promoters are activated by epigenetic drugs that facilitate the disruption of local repressor complexes.

Journal: Molecular pharmacology20090201

Title: Determination of a benzamide histone deacetylase inhibitor, MS-275, in human plasma by liquid chromatography with mass-spectrometric detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20090115

Title: Induction of Foxp3+ regulatory T cells with histone deacetylase inhibitors.

Journal: Cellular immunology20090101

Title: 'Shock and kill' effects of class I-selective histone deacetylase inhibitors in combination with the glutathione synthesis inhibitor buthionine sulfoximine in cell line models for HIV-1 quiescence.

Journal: Retrovirology20090101

Title: Anti-leukemia activity of MS-275 histone deacetylase inhibitor implicates 4-1BBL/4-1BB immunomodulatory functions.

Journal: PloS one20090101

Title: Defining the molecular action of HDAC inhibitors and synergism with androgen deprivation in ERG-positive prostate cancer.

Journal: International journal of cancer20081215

Title: Blockade of mTOR signaling potentiates the ability of histone deacetylase inhibitor to induce growth arrest and differentiation of acute myelogenous leukemia cells.

Journal: Leukemia20081201

Title: The histone-deacetylase inhibitor MS-275 and the CDK-inhibitor CYC-202 promote anti-tumor effects in hepatoma cell lines.

Journal: Oncology reports20081101

Title: MS-275, a novel histone deacetylase inhibitor with selectivity against HDAC1, induces degradation of FLT3 via inhibition of chaperone function of heat shock protein 90 in AML cells.

Journal: Leukemia research20080901

Title: Pharmacodynamic assessment of histone deacetylase inhibitors: infrared vibrational spectroscopic imaging of protein acetylation.

Journal: Analytical chemistry20080815

Title: Sp1-mediated TRAIL induction in chemosensitization.

Journal: Cancer research20080815

Title: Multicenter phase II trial of the histone deacetylase inhibitor pyridylmethyl-N-{4-[(2-aminophenyl)-carbamoyl]-benzyl}-carbamate in pretreated metastatic melanoma.

Journal: Melanoma research20080801

Title: A phase I and pharmacokinetic study of the oral histone deacetylase inhibitor, MS-275, in patients with refractory solid tumors and lymphomas.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20080715

Title: Inhibition of MEK/ERK signaling synergistically potentiates histone deacetylase inhibitor-induced growth arrest, apoptosis and acetylation of histone H3 on p21waf1 promoter in acute myelogenous leukemia cell.

Journal: Leukemia20080701

Title: p21(WAF1/CIP1) induction by 5-azacytosine nucleosides requires DNA damage.

Journal: Oncogene20080605

Title: Histone deacetylase inhibitors induce growth arrest, apoptosis, and differentiation in clear cell sarcoma models.

Journal: Molecular cancer therapeutics20080601

Title: Evaluation of the in vitro and in vivo antitumor activity of histone deacetylase inhibitors for the therapy of retinoblastoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20080515

Title: Potentiation of reactive oxygen species is a marker for synergistic cytotoxicity of MS-275 and 5-azacytidine in leukemic cells.

Journal: Leukemia research20080501

Title: Novel uracil-based 2-aminoanilide and 2-aminoanilide-like derivatives: histone deacetylase inhibition and in-cell activities.

Journal: Bioorganic & medicinal chemistry letters20080415

Title: MS-275 synergistically enhances the growth inhibitory effects of RAMBA VN/66-1 in hormone-insensitive PC-3 prostate cancer cells and tumours.

Journal: British journal of cancer20080408

Title: Identification of ligand features essential for HDACs inhibitors by pharmacophore modeling.

Journal: Journal of molecular graphics & modelling20080401

Title: Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts.

Journal: Bioorganic & medicinal chemistry20080315

Title: Probing the elusive catalytic activity of vertebrate class IIa histone deacetylases.

Journal: Bioorganic & medicinal chemistry letters20080315

Title: Acute-myeloid-leukemia-targeted toxins kill tumor cells by cell-type-specific mechanisms and synergize with TRAIL to allow manipulation of the extent and mechanism of tumor cell death.

Journal: Leukemia20080301

Title: Histone deacetylase inhibitors in lymphoma and solid malignancies.

Journal: Expert review of anticancer therapy20080301

Title: Regulation of arginase-1 expression in macrophages by a protein kinase A type I and histone deacetylase dependent pathway.

Journal: Journal of cellular biochemistry20080201

Title: Histone deacetylase inhibitors induce growth arrest and apoptosis of HTLV-1-infected T-cells via blockade of signaling by nuclear factor kappaB.

Journal: Leukemia research20080201

Title: Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors.

Journal: The Biochemical journal20080115

Title: Antiproliferative activities of a library of hybrids between indanones and HDAC inhibitor SAHA and MS-275 analogues.

Journal: Bioorganic & medicinal chemistry letters20071115

Title: Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity.

Journal: Journal of medicinal chemistry20071115

Title: Histone deacetylase inhibitors induce cell death and enhance the apoptosis-inducing activity of TRAIL in Ewing's sarcoma cells.

Journal: Journal of cancer research and clinical oncology20071101

Title: Histone deacetylase inhibitors suppress TF-kappaB-dependent agonist-driven tissue factor expression in endothelial cells and monocytes.

Journal: The Journal of biological chemistry20070928

Title: Phase I trial of MS-275, a histone deacetylase inhibitor, administered weekly in refractory solid tumors and lymphoid malignancies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070915

Title: Histone deacetylase inhibitor MS-275 alone or combined with bortezomib or sorafenib exhibits strong antiproliferative action in human cholangiocarcinoma cells.

Journal: World journal of gastroenterology20070907

Title: Trithiocarbonates: exploration of a new head group for HDAC inhibitors.

Journal: Bioorganic & medicinal chemistry letters20070901

Title: Relationship between embryonic histonic hyperacetylation and axial skeletal defects in mouse exposed to the three HDAC inhibitors apicidin, MS-275, and sodium butyrate.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20070801

Title: Antitumor activity of the histone deacetylase inhibitor MS-275 in prostate cancer models.

Journal: The Prostate20070801

Title: Synergistic in vivo antitumor effect of the histone deacetylase inhibitor MS-275 in combination with interleukin 2 in a murine model of renal cell carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070801

Title: Histone deacetylase inhibitors affect dendritic cell differentiation and immunogenicity.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070701

Title: Bispyridinium dienes: histone deacetylase inhibitors with selective activities.

Journal: Journal of medicinal chemistry20070517

Title: MAGE-A9 mRNA and protein expression in bladder cancer.

Journal: International journal of cancer20070515

Title: Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid.

Journal: Bioorganic & medicinal chemistry letters20070415

Title: Phase 1 and pharmacologic study of MS-275, a histone deacetylase inhibitor, in adults with refractory and relapsed acute leukemias.

Journal: Blood20070401

Title: Anti-rheumatic activities of histone deacetylase (HDAC) inhibitors in vivo in collagen-induced arthritis in rodents.

Journal: British journal of pharmacology20070401

Title: The histone deacetylase inhibitors depsipeptide and MS-275, enhance TRAIL gene therapy of LNCaP prostate cancer cells without adverse effects in normal prostate epithelial cells.

Journal: Cancer gene therapy20070301

Title: A liquid chromatography/tandem mass spectrometry assay to quantitate MS-275 in human plasma.

Journal: Journal of pharmaceutical and biomedical analysis20070117

Title: Measuring cytotoxicity: a new perspective on LC50.

Journal: Anticancer research20070101

Title: MS-275, a potent orally available inhibitor of histone deacetylases--the development of an anticancer agent.

Journal: The international journal of biochemistry & cell biology20070101

Title: HDAC inhibitors induce apoptosis in glucocorticoid-resistant acute lymphatic leukemia cells despite a switch from the extrinsic to the intrinsic death pathway.

Journal: The international journal of biochemistry & cell biology20070101

Title: Antiproliferative and proapoptotic effects of histone deacetylase inhibitors on gastrointestinal neuroendocrine tumor cells.

Journal: Endocrine-related cancer20061201

Title: Factors affecting the pharmacokinetic profile of MS-275, a novel histone deacetylase inhibitor, in patients with cancer.

Journal: Investigational new drugs20060901

Title: Substituted N-(2-aminophenyl)-benzamides, (E)-N-(2-aminophenyl)-acrylamides and their analogues: novel classes of histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters20060801

Title: Ex vivo therapy of malignant melanomas transplanted into organotypic brain slice cultures using inhibitors of histone deacetylases.

Journal: Acta neuropathologica20060801

Title: Experimental therapy of malignant gliomas using the inhibitor of histone deacetylase MS-275.

Journal: Molecular cancer therapeutics20060501

Title: Curcumin is an inhibitor of p300 histone acetylatransferase.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates))20060301

Title: Interspecies differences in plasma protein binding of MS-275, a novel histone deacetylase inhibitor.

Journal: Cancer chemotherapy and pharmacology20060201

Title: Anticancer activity of MS-275, a novel histone deacetylase inhibitor, against human endometrial cancer cells.

Journal: Anticancer research20060101

Title: Bombesin/gastrin-releasing peptide receptor antagonists increase the ability of histone deacetylase inhibitors to reduce lung cancer proliferation.

Journal: Journal of molecular neuroscience : MN20060101

Title: Histone deacetylase inhibitors in cancer therapy.

Journal: Cancer investigation20060101

Title: Histone deacetylase inhibitors promote osteoblast maturation.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research20051201

Title: Targeting epigenetic changes in acute myeloid leukemia.

Journal: Clinical advances in hematology & oncology : H&O20051101

Title: Early clinical data and potential clinical utility of novel histone deacetylase inhibitors in prostate cancer.

Journal: Clinical prostate cancer20050901

Title: Blockade of histone deacetylase inhibitor-induced RelA/p65 acetylation and NF-kappaB activation potentiates apoptosis in leukemia cells through a process mediated by oxidative damage, XIAP downregulation, and c-Jun N-terminal kinase 1 activation.

Journal: Molecular and cellular biology20050701

Title: [A new target of cancer therapy: advances in the study of histone deacetylase].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica20050701

Title: In vivo imaging of retinoic acid receptor beta2 transcriptional activation by the histone deacetylase inhibitor MS-275 in retinoid-resistant prostate cancer cells.

Journal: The Prostate20050615

Title: Phase I and pharmacokinetic study of MS-275, a histone deacetylase inhibitor, in patients with advanced and refractory solid tumors or lymphoma.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20050610

Title: Epigenetic modulation of retinoic acid receptor beta2 by the histone deacetylase inhibitor MS-275 in human renal cell carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20050501

Title: Histone deacetylase inhibitors and cancer: from cell biology to the clinic.

Journal: European journal of cell biology20050301

Title: Peak shape improvement of basic analytes in capillary liquid chromatography.

Journal: Journal of separation science20050201

Title: Histone deacetylase inhibitor pharmacodynamic analysis by multiparameter flow cytometry.

Journal: Annals of clinical and laboratory science20050101

Title: Enhancement of xenograft tumor radiosensitivity by the histone deacetylase inhibitor MS-275 and correlation with histone hyperacetylation.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20040915

Title: Histone deacetylase inhibitor enhances the anti-leukemic activity of an established nucleoside analogue.

Journal: Cancer biology & therapy20040801

Title: The histone deacetylase inhibitor MS-275 induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia cells.

Journal: Leukemia20040701

Title: Histone deacetylase inhibitors FK228, N-(2-aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl)amino- methyl]benzamide and m-carboxycinnamic acid bis-hydroxamide augment radiation-induced cell death in gastrointestinal adenocarcinoma cells.

Journal: International journal of cancer20040610

Title: Determination of MS-275, a novel histone deacetylase inhibitor, in human plasma by liquid chromatography-electrospray mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20040525

Title: The histone deacetylase inhibitor MS-275 interacts synergistically with fludarabine to induce apoptosis in human leukemia cells.

Journal: Cancer research20040401

Title: (2-amino-phenyl)-amides of omega-substituted alkanoic acids as new histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters20040105

Title: Enhanced radiation-induced cell killing and prolongation of gammaH2AX foci expression by the histone deacetylase inhibitor MS-275.

Journal: Cancer research20040101

Title: Synthesis and biological evaluation of 3-(4-substituted-phenyl)-N-hydroxy-2-propenamides, a new class of histone deacetylase inhibitors.

Journal: Journal of medicinal chemistry20031218

Title: Identification of novel isoform-selective inhibitors within class I histone deacetylases.

Journal: The Journal of pharmacology and experimental therapeutics20031101

Title: Inhibition of PI-3 kinase sensitizes human leukemic cells to histone deacetylase inhibitor-mediated apoptosis through p44/42 MAP kinase inactivation and abrogation of p21(CIP1/WAF1) induction rather than AKT inhibition.

Journal: Oncogene20030918

Title: The histone deacetylase inhibitor MS-275 promotes differentiation or apoptosis in human leukemia cells through a process regulated by generation of reactive oxygen species and induction of p21CIP1/WAF1 1.

Journal: Cancer research20030701

Title: Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin.

Journal: Blood20030301

Title: Gene expression profiling of multiple histone deacetylase (HDAC) inhibitors: defining a common gene set produced by HDAC inhibition in T24 and MDA carcinoma cell lines.

Journal: Molecular cancer therapeutics20030201

Title: Trifluoromethyl ketones as inhibitors of histone deacetylase.

Journal: Bioorganic & medicinal chemistry letters20021202

Title: MS-27-275, an inhibitor of histone deacetylase, has marked in vitro and in vivo antitumor activity against pediatric solid tumors.

Journal: Cancer research20021101

Title: Sulfonamide anilides, a novel class of histone deacetylase inhibitors, are antiproliferative against human tumors.

Journal: Cancer research20020801

Title: Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group.

Journal: Bioorganic & medicinal chemistry letters20020520

Title: Transcriptional regulation of the transforming growth factor beta type II receptor gene by histone acetyltransferase and deacetylase is mediated by NF-Y in human breast cancer cells.

Journal: The Journal of biological chemistry20020215

Title: MS-275, a histone deacetylase inhibitor, selectively induces transforming growth factor beta type II receptor expression in human breast cancer cells.

Journal: Cancer research20010201

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