Home Amines 404951-53-7
404951-53-7,MFCD09970778
Catalog No.:AA00BXT2

404951-53-7 | 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-

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10mg
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25mg
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00BXT2
Chemical Name:
2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-
CAS Number:
404951-53-7
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
MDL Number:
MFCD09970778
SMILES:
OCCN(Cc1ccc(cc1)/C=C/C(=O)NO)CCc1c[nH]c2c1cccc2
Properties
Computed Properties
 
Complexity:
505  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
9  
XLogP3:
2.6  

Literature

Title: Structure-based optimization of click-based histone deacetylase inhibitors.

Journal: European journal of medicinal chemistry 20110801

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

Journal: Journal of medicinal chemistry 20110714

Title: Restoring the functional immunogenicity of chronic lymphocytic leukemia using epigenetic modifiers.

Journal: Leukemia research 20110301

Title: Conformational refinement of hydroxamate-based histone deacetylase inhibitors and exploration of 3-piperidin-3-ylindole analogues of dacinostat (LAQ824).

Journal: Journal of medicinal chemistry 20100408

Title: Chemical phylogenetics of histone deacetylases.

Journal: Nature chemical biology 20100301

Title: Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091001

Title: Phase I pharmacokinetic and pharmacodynamic study of LAQ824, a hydroxamate histone deacetylase inhibitor with a heat shock protein-90 inhibitory profile, in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20081015

Title: Molecular and biologic characterization and drug sensitivity of pan-histone deacetylase inhibitor-resistant acute myeloid leukemia cells.

Journal: Blood 20081001

Title: Histone deacetylase inhibitors: apoptotic effects and clinical implications (Review).

Journal: International journal of oncology 20081001

Title: Role of histone deacetylase inhibitor-induced reactive oxygen species and DNA damage in LAQ-824/fludarabine antileukemic interactions.

Journal: Molecular cancer therapeutics 20081001

Title: Experimental treatment of pancreatic cancer with two novel histone deacetylase inhibitors.

Journal: World journal of gastroenterology 20080621

Title: Mitochondrial Bax translocation partially mediates synergistic cytotoxicity between histone deacetylase inhibitors and proteasome inhibitors in glioma cells.

Journal: Neuro-oncology 20080601

Title: Histone deacetylase inhibition and blockade of the glycolytic pathway synergistically induce glioblastoma cell death.

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

Title: Noninvasive magnetic resonance spectroscopic pharmacodynamic markers of a novel histone deacetylase inhibitor, LAQ824, in human colon carcinoma cells and xenografts.

Journal: Neoplasia (New York, N.Y.) 20080401

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

Journal: Bioorganic & medicinal chemistry letters 20080315

Title: Inhibitors of histone deacetylases induce tumor-selective cytotoxicity through modulating Aurora-A kinase.

Journal: Journal of molecular medicine (Berlin, Germany) 20080101

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

Journal: Journal of medicinal chemistry 20071115

Title: The multikinase inhibitor sorafenib potentiates TRAIL lethality in human leukemia cells in association with Mcl-1 and cFLIPL down-regulation.

Journal: Cancer research 20071001

Title: Inhibition of histone deacetylase for the treatment of biliary tract cancer: a new effective pharmacological approach.

Journal: World journal of gastroenterology 20070921

Title: HDAC inhibitors and cardiac safety.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070201

Title: Antitumor effect of the histone deacetylase inhibitor LAQ824 in combination with 13-cis-retinoic acid in human malignant melanoma.

Journal: Molecular cancer therapeutics 20070101

Title: Effect of histone deacetylase inhibitor LAQ824 on antineoplastic action of 5-Aza-2'-deoxycytidine (decitabine) on human breast carcinoma cells.

Journal: Cancer chemotherapy and pharmacology 20061101

Title: Class II histone deacetylases are associated with VHL-independent regulation of hypoxia-inducible factor 1 alpha.

Journal: Cancer research 20060901

Title: In vivo biological activity of the histone deacetylase inhibitor LAQ824 is detectable with 3'-deoxy-3'-[18F]fluorothymidine positron emission tomography.

Journal: Cancer research 20060801

Title: The histone deacetylase inhibitor LAQ824 induces human leukemia cell death through a process involving XIAP down-regulation, oxidative injury, and the acid sphingomyelinase-dependent generation of ceramide.

Journal: Molecular pharmacology 20060101

Title: Potentiation of the lethality of the histone deacetylase inhibitor LAQ824 by the cyclin-dependent kinase inhibitor roscovitine in human leukemia cells.

Journal: Molecular cancer therapeutics 20051101

Title: Chemical ablation of androgen receptor in prostate cancer cells by the histone deacetylase inhibitor LAQ824.

Journal: Molecular cancer therapeutics 20050901

Title: Histone deacetylase inhibitor NVP-LAQ824 has significant activity against myeloid leukemia cells in vitro and in vivo.

Journal: Leukemia 20041201

Title: The histone deacetylase inhibitor NVP-LAQ824 inhibits angiogenesis and has a greater antitumor effect in combination with the vascular endothelial growth factor receptor tyrosine kinase inhibitor PTK787/ZK222584.

Journal: Cancer research 20040915

Title: Superior activity of the combination of histone deacetylase inhibitor LAQ824 and the FLT-3 kinase inhibitor PKC412 against human acute myelogenous leukemia cells with mutant FLT-3.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040801

Title: In bcr-abl-positive myeloid cells resistant to conventional chemotherapeutic agents, expression of Par-4 increases sensitivity to imatinib (STI571) and histone deacetylase-inhibitors.

Journal: Biochemical pharmacology 20040701

Title: Use of a novel histone deacetylase inhibitor to induce apoptosis in cell lines of acute lymphoblastic leukemia.

Journal: Haematologica 20040401

Title: Selective growth inhibition of tumor cells by a novel histone deacetylase inhibitor, NVP-LAQ824.

Journal: Cancer research 20040115

Title: The discovery of NVP-LAQ824: from concept to clinic.

Journal: Current medicinal chemistry 20031101

Title: N-hydroxy-3-phenyl-2-propenamides as novel inhibitors of human histone deacetylase with in vivo antitumor activity: discovery of (2E)-N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide (NVP-LAQ824).

Journal: Journal of medicinal chemistry 20031009

Title: NVP-LAQ824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma.

Journal: Blood 20031001

Title: Histone deacetylase inhibitor LAQ824 down-regulates Her-2 and sensitizes human breast cancer cells to trastuzumab, taxotere, gemcitabine, and epothilone B.

Journal: Molecular cancer therapeutics 20031001

Title: Histone deacetylase inhibitor LAQ824 both lowers expression and promotes proteasomal degradation of Bcr-Abl and induces apoptosis of imatinib mesylate-sensitive or -refractory chronic myelogenous leukemia-blast crisis cells.

Journal: Cancer research 20030815

Title: Atadja P, et al. Selective growth inhibition of tumor cells by a novel histone deacetylase inhibitor, NVP-LAQ824. Cancer Res. 2004 Jan 15;64(2):689-95.

Title: Cho YS, et al. Conformational refinement of hydroxamate-based histone deacetylase inhibitors and exploration of 3-piperidin-3-ylindole analogues of dacinostat (LAQ824). J Med Chem. 2010 Apr 8;53(7):2952-63.

Title: Romanski A, et al. Deacetylase inhibitors modulate proliferation and self-renewal properties of leukemic stem and progenitor cells. Cell Cycle. 2012 Sep 1;11(17):3219-26.

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Tags:404951-53-7 Molecular Formula|404951-53-7 MDL|404951-53-7 SMILES|404951-53-7 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-