65673-63-4

Basic information

• Product Name: HA14-1
• Synonyms: 2-Amino-6-bromo-alpha-cyano-3-(ethoxycarbonyl)-(4H)-1-benzopyrane-4-aceticacidethylester;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 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 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
• CAS NO: 65673-63-4
• Molecular Formula: C17H17BrN2O5
• Molecular Weight: 409.23
• Product Categories: Caspases/Apoptosis;Inhibitor;Inhibitors
• Mol File: 65673-63-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 535.1°Cat760mmHg
• Flash Point: 277.4°C
• Appearance: /powder
• Density: 1.480
• Vapor Pressure: 1.59E-11mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: −20°C
• Solubility: DMSO: 26 mg/mL
• CAS DataBase Reference: HA14-1(CAS DataBase Reference)
• NIST Chemistry Reference: HA14-1(65673-63-4)
• EPA Substance Registry System: HA14-1(65673-63-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 65673-63-4(Hazardous Substances Data)

Usage

Uses

HA14-1 is a cell-permeable, nonpeptidic Bcl-2 inhibitor.

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.

InChI:InChI=1/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

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 1761-61-1 5-bromosalicyclaldehyde 

Relevant articles and documents

A small molecule inhibitor of Bcl-2, HA14-1, also inhibits ceramide glucosyltransferase

HA14-1 is a Bcl-2 inhibitor that is widely used for studies of apoptosis. In the course of searching for a ceramide glucosyltransferase inhibitor that catalyzes the first glycosylation step of glycosphingolipid synthesis, we unexpectedly found that HA-14-1 also has the ability to inhibit ceramide glucosyltransferase. The IC50 value of HA14-1 against ceramide glucosyltransferase is 4.5μM, which is lower than that reported for Bcl-2 in vitro. Kinetic analyses revealed that HA14-1 is a competitive and mixed-type inhibitor with respect to C6-NBD-ceramide and UDP-glucose, respectively.

Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine

Synthesis of 2-amino-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes has been accomplished by the reaction of salicylaldehyde, malononitrile, dialkyl/diphenylphosphites catalyzed by 1,1,3,3-tetramethylguanidine (TMG) under neat conditions at room tem

The synthesis of new, selected analogues of the pro-apoptotic and anticancer molecule HA 14-1

A new and versatile strategy has been developed towards HA 14-1 analogues, selectively modified on position 4 and/or on the primary amine function. An important aspect was the appropriate selection of the phenol protective group in the 5-bromosalicylaldeh