rel-Ethyl (αR,4R)-2-amino-6-bromo-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetate

HA14-1 is a Bcl-2/Bcl-XL antagonist. HA14-1 binds the designated pocket on Bcl-2 with the IC50 of ≈9 μM in competing with the Bcl-2 binding of Flu-BakBH3, and inhibits its function.

2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-1-benzopyran-3-carboxylic acid ethyl ester is a 1-benzopyran.

General procedure: TMG (3.5 mmol) was added to a mixture of SA (1 mmol), MN (1 mmol) and DAP (1 mmol) in neat condition. The resulting mixture was stirred at room temperature. After completion of the reaction (monitored by TLC), distilled water (15 mL) was added to the reaction mixture and stirring continued till a free flowing solid was obtained. It was filtered and then washed successively with water, n-hexane. The crude product was purified by recrystallization from ethanol solution. For this, the crude product was saturated in boiling ethanol and then the solution mixture was filtered when it was hot to remove the undissolved solid. The hot filtrate cooled down to room temperature to afford elemental analytically pure crystalline product. The similar experimental procedures were adopted for the synthesis of all the 2-amino-4H-chrormens.Ethyl-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA14-1) was purchased from Wako (Tokyo, Japan) or prepared by following an established procedure [12]. In short, 5-bromosalicylaldehyde was treated with ethyl cyanoacetate in the presence of MS3A in dry ethanol at room temperature to produce HA14-1 with a 55percent yield. Synthesized HA14-1 had inhibitory activity comparable with commercial HA14-1.General procedure: TMG (3.5 mmol) was added to a mixture of SA (1 mmol), MN (1 mmol) and DAP (1 mmol) in neat condition. The resulting mixture was stirred at room temperature. After completion of the reaction (monitored by TLC), distilled water (15 mL) was added to the reaction mixture and stirring continued till a free flowing solid was obtained. It was filtered and then washed successively with water, n-hexane. The crude product was purified by recrystallization from ethanol solution. For this, the crude product was saturated in boiling ethanol and then the solution mixture was filtered when it was hot to remove the undissolved solid. The hot filtrate cooled down to room temperature to afford elemental analytically pure crystalline product. The similar experimental procedures were adopted for the synthesis of all the 2-amino-4H-chrormens.Ethyl-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA14-1) was purchased from Wako (Tokyo, Japan) or prepared by following an established procedure [12]. In short, 5-bromosalicylaldehyde was treated with ethyl cyanoacetate in the presence of MS3A in dry ethanol at room temperature to produce HA14-1 with a 55percent yield. Synthesized HA14-1 had inhibitory activity comparable with commercial HA14-1.

Molecular Weight:409.2
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:408.03208
Monoisotopic Mass:408.03208
Topological Polar Surface Area:112
Heavy Atom Count:25
Complexity:611
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes