127061-45-4

Upstream product

• 111688-58-5 (3S,4S-trans)-3-carboxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (S)-α-methylbenzylamine salt 
• 111605-09-5 (3S,4S-trans)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 111688-58-5 (3R,4R-trans)-3-carboxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (R)-α-methylbenzylamine salt 
• 111605-06-2 (3R,4R-trans)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 111604-99-0 [1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid,dimethyl ester 
• 138383-10-5 1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 111605-05-1 [2-(2-amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid,dimethyl ester 
• 7443-25-6 dimethyl 2-(4-methoxybenzylidene)malonate 
• 6656-49-1 2-methyl-1-nitro-3-(trifluoromethyl)benzene 
• 138337-24-3 (3R,4R)-3-Hydroxy-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester 
• 138383-38-7 (3R,4R)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 138337-24-3 (3S,4S)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 138337-24-3 6-(trifluoromethyl)-1,3,4,5-tetrahydro-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 

Downstream Products

• 138335-51-0 (3S,4S-trans)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-1-<2-(dimethylamino)ethyl>-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 
• 138335-51-0 (3S,4R-cis)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-1-<2-(dimethylamino)ethyl>-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 

Relevant academic research and scientific papers

Benzazepinone calcium channel blockers. 4. Structure-activity overview and intracellular binding site

We have synthesized a series of benzazepinones (2) in order to determine the structure-activity relationships (SAR) for calcium channel blockers related to diltiazem. A prerequisite for calcium channel blocking activity in vitro and in vivo is the presenc

Benzazepinone calcium channel blockers. 2. Structure-activity and drug metabolism studies leading to potent antihypertensive agents. Comparison with benzothiazepinones

As part of a program to discover potent antihypertensive analogues of diltiazem (3a), we prepared 1-benzazepin-2-ones (4). Benzazepinones competitively displace radiolabeled diltiazem, and show the same absolute stereochemical preferences at the calcium channel receptor protein. Derivatives of 4 containing a trifluoromethyl substituent in the fused aromatic ring show potent and long-acting antihypertensive activity. Studies of the metabolism of 4 lead to the metabolically stable antihypertensive calcium channel blockers 5a and 5c. Benzazepinone 5a is a longer acting and more potent antihypertensive agent than the second generation diltiazem analogue TA-3090 (3e).

Chemoenzymatic synthesis of benzazepinone calcium channel blocking agents

The synthesis of a 6-trifluoromethyl-benzazepin-2-one derivative (3) from readily available nitro-toluene (4) is described.This synthetic route requires an enantio- and stereo-selective microbial reduction of racemic 13 to form (3R,4S)-cis-alcohol (10).Compound 3 is potent calcium channel blocking agent both in vitro and in vivo.