ChemicalBook > CAS DataBase List > HA14-1

HA14-1

Product Name
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
Formula Weight
409.23
MOL File
65673-63-4.mol
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HA14-1 Property

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
CAS DataBase Reference
65673-63-4
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
29322090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
14876
Product name
HA 14-1
Purity
≥98%
Packaging
5mg
Price
$25
Updated
2021/12/16
Cayman Chemical
Product number
14876
Product name
HA 14-1
Purity
≥98%
Packaging
10mg
Price
$48
Updated
2021/12/16
Cayman Chemical
Product number
14876
Product name
HA 14-1
Purity
≥98%
Packaging
25mg
Price
$113
Updated
2021/12/16
Cayman Chemical
Product number
14876
Product name
HA 14-1
Purity
≥98%
Packaging
50mg
Price
$163
Updated
2021/12/16
Tocris
Product number
1541
Product name
HA 14-1
Packaging
5
Price
$72
Updated
2021/12/16
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HA14-1 Chemical Properties,Usage,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

Raw materials

Preparation Products

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View Lastest Price from HA14-1 manufacturers

Career Henan Chemical Co
Product
HA14-1 65673-63-4
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

65673-63-4, HA14-1Related Search:

3-(5-BROMO-2-METHOXYPHENYL)PROPANOIC ACID 3-(3-BROMOPHENYL)PROPIONITRILE METHYL 3-(2-HYDROXYPHENYL)PROPIONATE ETHYL 2-CYANOVALERATE Ethyl 2-cyanopropanoate 3-Phenylglutaric acid 3-(3-Bromophenyl)propionic acid 3-(2-METHOXYPHENYL)PROPIONIC ACID 3-(3-Bromophenyl)-2-methylprop-1-ene HA14-1 ETHYL 2-CYANOBUTANOATE 3-(2-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER ethyl 2-cyano-3-phenyl-propanoate DIETHYL 2-METHYLGLUTARATE 2-Cyano-pentanedioic acid diethyl ester 3-(2-METHOXY-PHENYL)-PROPIONIC ACID ETHYL ESTER 3-(3-BROMO-PHENYL)-PROPIONIC ACID ETHYL ESTER 1-ALLYL-3-BROMOBENZENE

  • 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(4H)-1-benzopyrane-4-aceticacidethylester
  • ethyl 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
  • [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-aceticacidethylester
  • 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester
  • Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate
  • CS-392
  • Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate 97%
  • 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
  • (R)-ethyl 2-amino-6-bromo-4-((R)-1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
  • 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester HA 14-1
  • HA 14-1 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(alphaR,4R)-rel-4H-1-benzopyran-4-acetic acid ethyl ester
  • [Ethyl 2-amino-6-bromo-4-(1cyano-2-ethoxy-2-oxoethyl)-4H-chromene3-3carboxylate]
  • Ethyl2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylate97%
  • HA14-1;HA-14-1; HA 14-1
  • ethyl (4S)-2-amino-6-bromo-4-[(R)-cyano-ethoxycarbonyl-methyl]-4H-chromene-3-carboxylate
  • HA14-1
  • ETHYL [2-AMINO-6-BROMO-4-(1-CYANO-2-ETHOXY-2-OXOETHYL)]-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-
  • HA14-1 USP/EP/BP
  • rel-(R)-Ethyl 2-amino-6-bromo-4-((R)-1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate(relative)
  • rel-Ethyl (αR,4R)-2-amino-6-bromo-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetate
  • HA14-1/HA141
  • HA14-1, Bcl-2 inhibitor. BH-3 mimetic.
  • HA14-1, 10 mM in DMSO
  • 65673-63-4
  • C17H17BrN2O5
  • Apoptosis and Cell Cycle
  • BioChemical
  • Cell Biology
  • Apoptosis Inducers
  • Cell Signaling and Neuroscience
  • Inhibitors
  • Caspases/Apoptosis
  • Inhibitor