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ChemicalBook--->CAS DataBase List--->65673-63-4

65673-63-4

65673-63-4 Structure

65673-63-4 Structure
IdentificationBack Directory
[Name]

HA14-1
[CAS]

65673-63-4
[Synonyms]

CS-392
HA14-1
HA14-1 USP/EP/BP
HA14-1;HA-14-1; HA 14-1
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
ETHYL [2-AMINO-6-BROMO-4-(1-CYANO-2-ETHOXY-2-OXOETHYL)]-4H-CHROMENE-3-CARBOXYLATE
Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate
Ethyl2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate97%
(R)-ethyl 2-amino-6-bromo-4-((R)-1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate 97%
2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(4H)-1-benzopyrane-4-aceticacidethylester
ethyl (4S)-2-amino-6-bromo-4-[(R)-cyano-ethoxycarbonyl-methyl]-4H-chromene-3-carboxylate
2-AMINO-6-BROMO-ALPHA-CYANO-3-(ETHOXYCARBONYL)-4H-1-BENZOPYRAN-4-ACETIC ACID ETHYL ESTER
4H-1-Benzopyran-4-acetic acid, 2-amino-6-bromo-α-cyano-3-(ethoxycarbonyl)-, ethyl ester, (αR,4R)-rel-
rel-(R)-Ethyl 2-amino-6-bromo-4-((R)-1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate(relative)
2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester
HA 14-1 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester
2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester HA 14-1
[Ethyl 2-amino-6-bromo-4-(1cyano-2-ethoxy-2-oxoethyl)-4H-chromene3-3carboxylate], Ethyl [2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)]-4H-chromene-3-carboxylate
2-Amino-6-bromo-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic acid ethyl ester, Ethyl [2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)]-4H-chromene-3-carboxylate
HA 14-1, Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate, 2-[2-Amino-6-bromo-3-(ethoxycarbonyl)-4H-chromen-4-yl]-3-ethoxy-3-oxopropanenitrile
[Molecular Formula]

C17H17BrN2O5
[MDL Number]

MFCD00218213
[MOL File]

65673-63-4.mol
[Molecular Weight]

409.23
Chemical PropertiesBack Directory
[Melting point ]

105 °C
[density ]

1.480
[storage temp. ]

−20°C
[solubility ]

DMSO: 26 mg/mL
[form ]

powder
[color ]

White to light yellow
[CAS DataBase Reference]

65673-63-4
Safety DataBack Directory
[Safety Statements ]

22-24/25
[WGK Germany ]

3
[HS Code ]

29322090
Hazard InformationBack Directory
[Uses]

Cell permeable, low molecular weight Bcl-2 ligand. Antagonizes the function of Bcl-2 and induces apoptosis. In HL-60 cells, HA4-1 (50μM and 4h incubation) induced apoptosis of more than 90% of the cells. Apoptosis is blocked by ZVAD-FM. IC50 = ~9μM for competition with Flu-BakBH3 binding to Bcl-2.
[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.
[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
[storage]

Desiccate at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

HA14-1(65673-63-4)MS
HA14-1(65673-63-4)1HNMR
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