313750-60-6

Basic information

• Product Name: 1H-1-Benzazepine-4-carboxylic acid, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-, methyl ester
• CAS NO: 313750-60-6
• Molecular Formula: C24H29NO4
• Molecular Weight: 395.499
• Mol File: 313750-60-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-1-Benzazepine-4-carboxylic acid, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1-Benzazepine-4-carboxylic acid, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-, methyl ester(313750-60-6)
• EPA Substance Registry System: 1H-1-Benzazepine-4-carboxylic acid, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-, methyl ester(313750-60-6)

Safety Data

• Hazardous Substances Data: 313750-60-6(Hazardous Substances Data)

Upstream product

• 313724-44-6 methyl 7-bromo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylate 
• 313735-42-1 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 313724-31-1 methyl 7-bromo-1-(t-butoxycarbonyl)-1,2,3,4-tetrahydro-1-benzazepin-5-one-4-carboxylate 
• 313724-37-7 methyl 7-bromo-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 313724-26-4 7-bromo-1-(t-butoxycarbonyl)-1,2,3,4-tetrahydro-1-benzazepin-5-one 
• 39255-24-8 1-bromo-4-[2-(butoxy)ethoxy]benzene 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 10503-96-5 1-(2-chloroethoxy)butane 
• 3951-89-1 7-bromo-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one 
• 279262-28-1 {4-[2-(butoxy)ethoxy]phenyl}boronic acid 

Downstream Products

• 313730-15-3 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-phenyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 313753-40-1 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-[(1-methyl-1H-pyrazol-5-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 313738-17-9 methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(tetrazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate 
• 313730-66-4 methyl 7-[4-(2-butoxyethoxy)phenyl]-1-chloroacetyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate 

Relevant articles and documents

Orally active CCR5 antagonists as anti-HIV-1 agents: Synthesis and biological activity of 1-benzothiepine 1,1-dioxide and 1-benzazepine derivatives containing a tertiary amine moiety

The search for orally active CCR5 antagonists was performed by chemical modification of the 1-benzothiepine 1,1-dioxide 3 and 1-benzazepine 4 lead compounds containing a tertiary amine moiety. Replacement of methyl group with a 2-(C2-4 alkoxy)ethoxy group at the 4-position on the 7-phenyl group of the 1-benzothiepine ring resulted in both enhanced activity and significant improvement in the pharmacokinetic properties upon oral administration in rats. Introduction of C2-4 alkyl, phenyl or (hetero)arylmethyl groups as the 1-substituent on the 1-benzazepine ring together with the 2-(butoxy)ethoxy group led to further increase of activity. Among the 1- benzazepine derivatives, the isobutyl (6i), benzyl (6o) or 1-methylpyrazol-4-ylmethyl (6s) compounds were found to exhibit highly potent inhibitory effects, equivalent to the injectable CCR5 antagonist 1, in the HIV-1 envelopemediated membrane fusion assay. In particular, compound 6s showed the most potent CCR5 antagonistic activity (IC50=2.7 nM) and inhibitory effect (IC50=1.2 nM) on membrane fusion, together with good pharmacokinetic properties in rats. The synthesis of 1-benzothiepine 1,1-dioxide and 1-benzazepine derivatives and their biological activity are described.