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

Packsize	Purity	Availability	Price	Discounted Price
1mg	98%	in stock	$17.00	$12.00
10mg	98%	in stock	$38.00	$27.00
50mg	98%	in stock	$58.00	$41.00
100mg	98%	in stock	$98.00	$69.00
250mg	98%	in stock	$165.00	$116.00

Description

• Catalog Number: AH13150
• 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

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

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

  British journal of cancer 20120214

• Apoptosis sensitizers enhance cytotoxicity in hepatoblastoma cells.

  Pediatric surgery international 20120201

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

  Free radical biology & medicine 20120115

• BH3 mimetics activate multiple pro-autophagic pathways.

  Oncogene 20110915

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

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

• Transient mitochondrial permeability transition pore opening after neonatal cardioplegic arrest.

  The Journal of thoracic and cardiovascular surgery 20110401

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

  FEBS letters 20110323

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

  Bioorganic & medicinal chemistry letters 20101101

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

  Free radical biology & medicine 20101015

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

  Apoptosis : an international journal on programmed cell death 20101001

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

  Pflugers Archiv : European journal of physiology 20101001

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

  Cancer letters 20100601

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

  Cancer letters 20100428

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

  Apoptosis : an international journal on programmed cell death 20100401

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

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

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

  Neuroscience letters 20100104

• 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.

  Breast cancer research and treatment 20100101

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

  Journal of neuroscience research 20091201

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

  Molecular cancer therapeutics 20091101

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

  Biochemical and biophysical research communications 20091030

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

  Molecular pharmacology 20090901

• 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.

  Brain research 20090804

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

  Cancer biology & therapy 20090501

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

  Cancer biology & therapy 20090501

• 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.

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

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

  Biochemical pharmacology 20081015

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

  Cell calcium 20081001

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

  Neoplasia (New York, N.Y.) 20080801

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

  Yao xue xue bao = Acta pharmaceutica Sinica 20080701

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

  Neuroscience letters 20080523

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

  European journal of haematology 20080501

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

  Oncogene 20080306

• 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.

  Cancer letters 20080208

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

  Photochemistry and photobiology 20080101

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

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

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

  The Journal of biological chemistry 20071214

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

  Leukemia research 20071201

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

  Cancer letters 20070808

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

  Leukemia research 20070601

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

  Cancer letters 20070508

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

  British journal of cancer 20070226

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

  Oncogene 20070201

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

  Neurobiology of disease 20070201

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

  Oncology reports 20070201

• 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.

  Molecular pharmaceutics 20070101

• 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 of medicinal chemistry 20061228

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

  Experimental hematology 20061201

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

  Leukemia research 20060901

• Protection of Bcl-2 by salubrinal.

  Biochemical and biophysical research communications 20060811

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

  Biochemical and biophysical research communications 20060630

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

  Cancer research 20060301

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

  Current eye research 20060101

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

  Cell communication & adhesion 20060101

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

  The Journal of pharmacology and experimental therapeutics 20051201

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

  Cell death and differentiation 20051101

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

  Molecular cancer therapeutics 20051001

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

  Journal of neurochemistry 20050701

• 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.

  Cancer letters 20050428

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

  Cancer research 20050215

• 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.

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

• 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.

  Molecular cancer therapeutics 20041201

• 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.

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

• 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 of hepatology 20041101

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

  The Journal of biological chemistry 20040813

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

  Cell death and differentiation 20040801

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

  Cancer research 20040515

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

  The Journal of biological chemistry 20040430

• 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.

  Molecular pharmacology 20040401

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

  Leukemia 20040301

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

  Leukemia 20031101

• Bcl-2-related proteins as drug targets.

  Current medicinal chemistry 20030801

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

  Current medicinal chemistry. Anti-cancer agents 20030501

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

  Molecular cancer therapeutics 20021001

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

  Photochemistry and photobiology 20020901

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

  Blood 20020501