Home Amines 65673-63-4
65673-63-4,MFCD00218213
Catalog No.:AA00FACI

65673-63-4 | Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4h-chromene-3-carboxylate

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10mg
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50mg
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100mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00FACI
Chemical Name:
Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4h-chromene-3-carboxylate
CAS Number:
65673-63-4
Molecular Formula:
C17H17BrN2O5
Molecular Weight:
409.2313
MDL Number:
MFCD00218213
SMILES:
CCOC(=O)[C@H]([C@H]1C(=C(N)Oc2c1cc(Br)cc2)C(=O)OCC)C#N
NSC Number:
720569
Properties
Properties
 
BP:
535.1±50.0°C at 760 mmHg  
Form:
Solid  
MP:
105℃  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
611  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
7  
Undefined Atom Stereocenter Count:
2  
XLogP3:
3  

Literature

Title: The BH3 mimetic HA14-1 enhances 5-fluorouracil-induced autophagy and type II cell death in oesophageal cancer cells.

Journal: British journal of cancer 20120214

Title: Apoptosis sensitizers enhance cytotoxicity in hepatoblastoma cells.

Journal: Pediatric surgery international 20120201

Title: Bcl-2 is a novel interacting partner for the 2-oxoglutarate carrier and a key regulator of mitochondrial glutathione.

Journal: Free radical biology & medicine 20120115

Title: BH3 mimetics activate multiple pro-autophagic pathways.

Journal: Oncogene 20110915

Title: Mitochondrial targeting by use of lipid nanocapsules loaded with SV30, an analogue of the small-molecule Bcl-2 inhibitor HA14-1.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20110410

Title: Transient mitochondrial permeability transition pore opening after neonatal cardioplegic arrest.

Journal: The Journal of thoracic and cardiovascular surgery 20110401

Title: Blockade of electron transport during ischemia preserves bcl-2 and inhibits opening of the mitochondrial permeability transition pore.

Journal: FEBS letters 20110323

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Bcl-2 sustains hormetic response by inducing Nrf-2 nuclear translocation in L929 mouse fibroblasts.

Journal: Free radical biology & medicine 20101015

Title: Bcl-2 inhibits apoptosis by increasing the time-to-death and intrinsic cell-to-cell variations in the mitochondrial pathway of cell death.

Journal: Apoptosis : an international journal on programmed cell death 20101001

Title: Inhibitors of Bcl-2 protein family deplete ER Ca2+ stores in pancreatic acinar cells.

Journal: Pflugers Archiv : European journal of physiology 20101001

Title: HA14-1 sensitizes TNF-alpha-induced apoptosis via inhibition of the NF-kappaB signaling pathway: involvement of reactive oxygen species and JNK.

Journal: Cancer letters 20100601

Title: Bisphenol A and estradiol are equipotent in antagonizing cisplatin-induced cytotoxicity in breast cancer cells.

Journal: Cancer letters 20100428

Title: Neuroglobin protects nerve cells from apoptosis by inhibiting the intrinsic pathway of cell death.

Journal: Apoptosis : an international journal on programmed cell death 20100401

Title: Induction of apoptosis by esculetin in human leukemia U937 cells: roles of Bcl-2 and extracellular-regulated kinase signaling.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20100301

Title: Repeated cocaine administration increases B-cell leukemia/lymphoma 2 phosphorylation in the rat dorsal striatum.

Journal: Neuroscience letters 20100104

Title: Small inhibitor of Bcl-2, HA14-1, selectively enhanced the apoptotic effect of cisplatin by modulating Bcl-2 family members in MDA-MB-231 breast cancer cells.

Journal: Breast cancer research and treatment 20100101

Title: Down-regulation of Bcl-2 enhances autophagy activation and cell death induced by mitochondrial dysfunction in rat striatum.

Journal: Journal of neuroscience research 20091201

Title: Mcl-1 is an important determinant of the apoptotic response to the BH3-mimetic molecule HA14-1 in cisplatin-resistant ovarian carcinoma cells.

Journal: Molecular cancer therapeutics 20091101

Title: Bcl-2 inhibitor and apigenin worked synergistically in human malignant neuroblastoma cell lines and increased apoptosis with activation of extrinsic and intrinsic pathways.

Journal: Biochemical and biophysical research communications 20091030

Title: Dual mechanisms of sHA 14-1 in inducing cell death through endoplasmic reticulum and mitochondria.

Journal: Molecular pharmacology 20090901

Title: Bcl-2 inhibitor HA14-1 and genistein together adeptly down regulated survival factors and activated cysteine proteases for apoptosis in human malignant neuroblastoma SK-N-BE2 and SH-SY5Y cells.

Journal: Brain research 20090804

Title: Bcl-2 antagonists interact synergistically with bortezomib in DLBCL cells in association with JNK activation and induction of ER stress.

Journal: Cancer biology & therapy 20090501

Title: Piling up the JNK: drug synergy through ER stress.

Journal: Cancer biology & therapy 20090501

Title: Naringenin-induced apoptosis is attenuated by Bcl-2 but restored by the small molecule Bcl-2 inhibitor, HA 14-1, in human leukemia U937 cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20090301

Title: Bcl-2 family members as molecular targets in cancer therapy.

Journal: Biochemical pharmacology 20081015

Title: Bcl2 mitigates Ca2+ entry and mitochondrial Ca2+ overload through downregulation of L-type Ca2+ channels in PC12 cells.

Journal: Cell calcium 20081001

Title: BH3 mimetics reactivate autophagic cell death in anoxia-resistant malignant glioma cells.

Journal: Neoplasia (New York, N.Y.) 20080801

Title: [Progress in small-molecule inhibitors of Bcl-2 family proteins].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080701

Title: Effects of selective Bcl-2 inhibitor HA14-1 treatments on functional activity of magnocellular vasopressinergic neurons of rat hypothalamus.

Journal: Neuroscience letters 20080523

Title: Combined proteasome and Bcl-2 inhibition stimulates apoptosis and inhibits growth in EBV-transformed lymphocytes: a potential therapeutic approach to EBV-associated lymphoproliferative diseases.

Journal: European journal of haematology 20080501

Title: RhoA prevents apoptosis during zebrafish embryogenesis through activation of Mek/Erk pathway.

Journal: Oncogene 20080306

Title: sHA 14-1, a stable and ROS-free antagonist against anti-apoptotic Bcl-2 proteins, bypasses drug resistances and synergizes cancer therapies in human leukemia cell.

Journal: Cancer letters 20080208

Title: The Bcl-2 antagonist HA14-1 forms a fluorescent albumin complex that can be mistaken for several oxidized ROS probes.

Journal: Photochemistry and photobiology 20080101

Title: HA14-1 is able to reconstitute the impaired mitochondrial pathway of apoptosis in renal cell carcinoma cell lines.

Journal: Cellular oncology : the official journal of the International Society for Cellular Oncology 20080101

Title: Shp2E76K mutant confers cytokine-independent survival of TF-1 myeloid cells by up-regulating Bcl-XL.

Journal: The Journal of biological chemistry 20071214

Title: Brefeldin A triggers apoptosis associated with mitochondrial breach and enhances HA14-1- and anti-Fas-mediated cell killing in follicular lymphoma cells.

Journal: Leukemia research 20071201

Title: Exploitation of drug-induced Bcl-2 overexpression for restoring normal apoptosis function: a promising new approach to the treatment of multidrug resistant cancer.

Journal: Cancer letters 20070808

Title: HA14-1, a small molecule inhibitor of Bcl-2, bypasses chemoresistance in leukaemia cells.

Journal: Leukemia research 20070601

Title: Initiation of apoptosis and autophagy by the Bcl-2 antagonist HA14-1.

Journal: Cancer letters 20070508

Title: Small-molecule Bcl-2 inhibitors sensitise tumour cells to immune-mediated destruction.

Journal: British journal of cancer 20070226

Title: Overcoming the radioresistance of prostate cancer cells with a novel Bcl-2 inhibitor.

Journal: Oncogene 20070201

Title: Bcl-2 upregulation and neuroprotection in guinea pig brain following chronic simvastatin treatment.

Journal: Neurobiology of disease 20070201

Title: Synergistic inhibition of breast cancer cell lines with a dual inhibitor of EGFR-HER-2/neu and a Bcl-2 inhibitor.

Journal: Oncology reports 20070201

Title: Ethyl-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H- chromene-3-carboxylate (HA 14-1), a prototype small-molecule antagonist against antiapoptotic Bcl-2 proteins, decomposes to generate reactive oxygen species that induce apoptosis.

Journal: Molecular pharmaceutics 20070101

Title: Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer.

Journal: Journal of medicinal chemistry 20061228

Title: Bcl-2 inhibitors induce apoptosis in chronic lymphocytic leukemia cells.

Journal: Experimental hematology 20061201

Title: Multiparametric analysis of HA14-1-induced apoptosis in follicular lymphoma cells.

Journal: Leukemia research 20060901

Title: Protection of Bcl-2 by salubrinal.

Journal: Biochemical and biophysical research communications 20060811

Title: Ceramide response post-photodamage is absent after treatment with HA14-1.

Journal: Biochemical and biophysical research communications 20060630

Title: The small organic compound HA14-1 prevents Bcl-2 interaction with Bax to sensitize malignant glioma cells to induction of cell death.

Journal: Cancer research 20060301

Title: Protective effect of donepezil on retinal ganglion cells in vitro and in vivo.

Journal: Current eye research 20060101

Title: Inhibition of CD95-mediated apoptosis through beta 1 integrin in the HSG epithelial cell line.

Journal: Cell communication & adhesion 20060101

Title: Unequal neuroprotection afforded by the acetylcholinesterase inhibitors galantamine, donepezil, and rivastigmine in SH-SY5Y neuroblastoma cells: role of nicotinic receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20051201

Title: Involvement of hTERT in apoptosis induced by interference with Bcl-2 expression and function.

Journal: Cell death and differentiation 20051101

Title: Sulindac sulfide-induced apoptosis is enhanced by a small-molecule Bcl-2 inhibitor and by TRAIL in human colon cancer cells overexpressing Bcl-2.

Journal: Molecular cancer therapeutics 20051001

Title: Distinct mechanisms of neuronal apoptosis are triggered by antagonism of Bcl-2/Bcl-x(L) versus induction of the BH3-only protein Bim.

Journal: Journal of neurochemistry 20050701

Title: Susceptibility of myelomonocytic leukemia U937 cells to the induction of apoptosis by the non-peptidic Bcl-2 ligand HA14-1 is cell cycle phase-dependent.

Journal: Cancer letters 20050428

Title: Mitotic arrest deficient 2 expression induces chemosensitization to a DNA-damaging agent, cisplatin, in nasopharyngeal carcinoma cells.

Journal: Cancer research 20050215

Title: Tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis is inhibited by Bcl-2 but restored by the small molecule Bcl-2 inhibitor, HA 14-1, in human colon cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041215

Title: The small-molecule Bcl-2 inhibitor HA14-1 interacts synergistically with flavopiridol to induce mitochondrial injury and apoptosis in human myeloma cells through a free radical-dependent and Jun NH2-terminal kinase-dependent mechanism.

Journal: Molecular cancer therapeutics 20041201

Title: Trastuzumab down-regulates Bcl-2 expression and potentiates apoptosis induction by Bcl-2/Bcl-XL bispecific antisense oligonucleotides in HER-2 gene--amplified breast cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041115

Title: Peripheral benzodiazepine receptor ligands induce apoptosis and cell cycle arrest in human hepatocellular carcinoma cells and enhance chemosensitivity to paclitaxel, docetaxel, doxorubicin and the Bcl-2 inhibitor HA14-1.

Journal: Journal of hepatology 20041101

Title: A Bcr/Abl-independent, Lyn-dependent form of imatinib mesylate (STI-571) resistance is associated with altered expression of Bcl-2.

Journal: The Journal of biological chemistry 20040813

Title: A mechanism for the proapoptotic activity of ursodeoxycholic acid: effects on Bcl-2 conformation.

Journal: Cell death and differentiation 20040801

Title: Bcl-2 inhibitors sensitize tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis by uncoupling of mitochondrial respiration in human leukemic CEM cells.

Journal: Cancer research 20040515

Title: Critical upstream signals of cytochrome C release induced by a novel Bcl-2 inhibitor.

Journal: The Journal of biological chemistry 20040430

Title: Differential susceptibilities of murine hepatoma 1c1c7 and Tao cells to the lysosomal photosensitizer NPe6: influence of aryl hydrocarbon receptor on lysosomal fragility and protease contents.

Journal: Molecular pharmacology 20040401

Title: PKC alpha mediates chemoresistance in acute lymphoblastic leukemia through effects on Bcl2 phosphorylation.

Journal: Leukemia 20040301

Title: HA14-1 selectively induces apoptosis in Bcl-2-overexpressing leukemia/lymphoma cells, and enhances cytarabine-induced cell death.

Journal: Leukemia 20031101

Title: Bcl-2-related proteins as drug targets.

Journal: Current medicinal chemistry 20030801

Title: The BCL2-family of protein ligands as cancer drugs: the next generation of therapeutics.

Journal: Current medicinal chemistry. Anti-cancer agents 20030501

Title: The apoptotic effect of HA14-1, a Bcl-2-interacting small molecular compound, requires Bax translocation and is enhanced by PK11195.

Journal: Molecular cancer therapeutics 20021001

Title: Apoptotic response to photodynamic therapy versus the Bcl-2 antagonist HA14-1.

Journal: Photochemistry and photobiology 20020901

Title: Synergistic induction of apoptosis by simultaneous disruption of the Bcl-2 and MEK/MAPK pathways in acute myelogenous leukemia.

Journal: Blood 20020501

Title: Wang JL, et al. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7124-9.

Title: Kessel D, et al. Initiation of apoptosis and autophagy by the Bcl-2 antagonist HA14-1. Cancer Lett. 2007 May 8;249(2):294-9.

Title: Manero F, et al. The small organic compound HA14-1 prevents Bcl-2 interaction with Bax to sensitize malignant glioma cells to induction of cell death. Cancer Res. 2006 Mar 1;66(5):2757-64.

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Tags:65673-63-4 Molecular Formula|65673-63-4 MDL|65673-63-4 SMILES|65673-63-4 Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4h-chromene-3-carboxylate