HA14-1
- CAS No.
- 65673-63-4
- Chemical Name:
- HA14-1
- Synonyms
- CS-392;HA14-1;HA14-1/HA141;HA14-1 USP/EP/BP;HA14-1, 10 mM in DMSO;HA14-1;HA-14-1; HA 14-1;HA14-1, Bcl-2 inhibitor. BH-3 mimetic.;ethyl 6-broMo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chroMene-3-carboxylate;[Ethyl 2-amino-6-bromo-4-(1cyano-2-ethoxy-2-oxoethyl)-4H-chromene3-3carboxylate];2-Amino-6-bromo-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-aceticacidethylester
- CBNumber:
- CB2170185
- Molecular Formula:
- C17H17BrN2O5
- Molecular Weight:
- 409.23
- MDL Number:
- MFCD00218213
- MOL File:
- 65673-63-4.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Product description | Number | Pack Size | Price |
| HA 14-1 ≥98% | 14876 | 10mg | $48 |
| HA 14-1 ≥98% | 14876 | 5mg | $25 |
| HA 14-1 | Axon2007 | 10mg | $82.5 |
| HA 14-1 | Axon2007 | 50mg | $302.5 |
| Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate | 083677 | 50.00g | $65 |
| More product size | |||
| Melting point | 105 °C |
|---|---|
| Density | 1.480 |
| storage temp. | Keep in dark place,Sealed in dry,Store in freezer, under -20°C |
| solubility | DMSO: 26 mg/mL |
| form | powder |
| color | White to light yellow |
| InChI | 1S/C17H17BrN2O5/c1-3-23-16(21)11(8-19)13-10-7-9(18)5-6-12(10)25-15(20)14(13)17(22)24-4-2/h5-7,11,13H,3-4,20H2,1-2H3 |
| InChIKey | SXJDCULZDFWMJC-UHFFFAOYSA-N |
| SMILES | CCOC(=O)C(C#N)C1c2cc(Br)ccc2OC(N)=C1C(=O)OCC |
| CAS DataBase Reference | 65673-63-4 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302+H312+H332-H315-H319-H335 | |||||||||
| Precautionary statements | P280 | |||||||||
| PPE | Eyeshields, Gloves, type N95 (US) | |||||||||
| Safety Statements | 22-24/25 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29322090 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| NFPA 704 |
|
HA14-1 price More Price(42)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 14876 | HA 14-1 ≥98% | 65673-63-4 | 10mg | $48 | 2021-12-16 | Buy |
| Cayman Chemical | 14876 | HA 14-1 ≥98% | 65673-63-4 | 5mg | $25 | 2021-12-16 | Buy |
| Axon Medchem | Axon2007 | HA 14-1 | 10mg | $82.5 | 2026-05-19 | Buy | |
| Axon Medchem | Axon2007 | HA 14-1 | 50mg | $302.5 | 2026-05-19 | Buy | |
| Matrix Scientific | 083677 | Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate | 65673-63-4 | 50.00g | $65 | 2026-05-18 | Buy |
HA14-1 Chemical Properties,Uses,Production
Uses
HA14-1 is a cell-permeable, nonpeptidic Bcl-2 inhibitor.
Definition
ChEBI: 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylic acid ethyl ester is a 1-benzopyran.
Biological Activity
Cell-permeable inhibitor of Bcl-2 protein (IC 50 ~ 9 μ M); acts by binding to the surface pocket. Disrupts Bax/Bcl-2 interaction and induces apoptosis of tumor cells.
Biochem/physiol Actions
HA 14-1 is a nonpeptide apoptosis inducer; Bcl-2 antagonist.
Synthesis
105-56-6
1761-61-1
65673-63-4
GENERAL METHODS: 1,1,3,3-Tetramethylguanidine (TMG, 3.5 mmol) was added to a mixture of 5-bromosalicylaldehyde (SA, 1 mmol), ethyl cyanoacetate (MN, 1 mmol), and 2,3-diaminopyridine (DAP, 1 mmol) under pure conditions. The reaction mixture was stirred at room temperature and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, distilled water (15 mL) was added to the reaction mixture and stirring was continued until a free-flowing solid was formed. The solid was collected by filtration and washed sequentially with water and hexane. The crude product was purified by recrystallization from ethanol solution: the crude product was dissolved in boiling ethanol to saturation and hot filtered to remove undissolved solid. The hot filtrate was cooled to room temperature to give an elementally analytically pure crystalline product, rel-(αR,4R)-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-carbonyl)-4H-benzofuran-3-carboxylic acid. Similar experimental procedures were used to synthesize all 2-amino-4H-benzofuran derivatives.
in vivo
Swiss nude mice are challenged with BeGBM cells (104 injected s.c.). HA14-1 (400 nmol) in 100 μL free RPMI 1640-50% DMSO, or the carrier alone, is given at the site of injection once weekly from day 2 following cell injection. HA14-1 treatment does not have any significant effect on the growth of glioblastoma tumors in immunodeficient mice as monitored twice weekly by measuring the volume of the expanding tumors. Moreover, no gross organ toxicity or weight loss can be detected in mice receiving such treatment. To analyze whether HA14-1 treatment might enhance the efficiency of another antitumoral treatment, Swiss nude mice challenged with human glioblastoma multiforme cells are also given i.p. low doses of Etoposide (2.5 mg/kg in 200 μL of 0.9% NaCl 5 days a week from day 2 following cell injection) together with HA14-1 or mock treatment. Whereas Etoposide treatment is insufficient by itself to restrain the growth of glioblastoma cells, its combination with HA14-1 leads to a significant restrain on tumor growth as judged by the ability of the combined treatment to increase the doubling time of the tumor volume[3].
IC 50
Bcl-2: 9 μM (IC50); Bcl-xL
References
[1] Tetrahedron Letters, 2005, vol. 46, # 20, p. 3497 - 3499
[2] RSC Advances, 2015, vol. 5, # 80, p. 65526 - 65531
[3] Tetrahedron, 2013, vol. 69, # 49, p. 10544 - 10551
[4] Tetrahedron Letters, 2006, vol. 47, # 43, p. 7629 - 7633
[5] Russian Chemical Bulletin, 2008, vol. 57, # 3, p. 595 - 600
HA14-1 Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 33024 | 60 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29816 | 58 |
| SHANGHAI T&W PHARMACEUTICAL CO., LTD. | +86-021-61551413 +8618813727289 | contact@trustwe.com | China | 5742 | 58 |
| Tianjin Xinshengjiahe Science & Technology Development Co,.Ltd | +86-86-22-87899925 +86-8618522618860 | 18522618860@163.com | China | 694 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354; +17819995354 | marketing@targetmol.com | United States | 32467 | 58 |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 18895 | 58 |
| Zhejiang J&C Biological Technology Co.,Limited | +1-2135480471 +1-2135480471; | sales@sarms4muscle.com | China | 10473 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6391 | 58 |
| HANGZHOU LEAP CHEM CO., LTD. | +86-571-87711850 | market18@leapchem.com | China | 24597 | 58 |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8615965530500 | nickzhang@hangyubiotech.com | China | 9953 | 58 |
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