597583-16-9

Basic information

• Product Name: 1H-1-Benzazepine-4-carbonyl chloride, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-(2-methylpropyl)-
• CAS NO: 597583-16-9
• Molecular Formula: C27H34ClNO3
• Molecular Weight: 456.025
• Mol File: 597583-16-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-1-Benzazepine-4-carbonyl chloride, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1-Benzazepine-4-carbonyl chloride, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-(2-methylpropyl)-(597583-16-9)
• EPA Substance Registry System: 1H-1-Benzazepine-4-carbonyl chloride, 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-(2-methylpropyl)-(597583-16-9)

Safety Data

• Hazardous Substances Data: 597583-16-9(Hazardous Substances Data)

Upstream product

• 313735-42-1 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 313724-44-6 methyl 7-bromo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylate 
• 313736-13-9 methyl 7-bromo-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 597583-14-7 7-bromo-1-isobutyl-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid 
• 313736-34-4 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 313736-28-6 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 313724-31-1 methyl 7-bromo-1-(t-butoxycarbonyl)-1,2,3,4-tetrahydro-1-benzazepin-5-one-4-carboxylate 
• 313724-26-4 7-bromo-1-(t-butoxycarbonyl)-1,2,3,4-tetrahydro-1-benzazepin-5-one 
• 279262-28-1 {4-[2-(butoxy)ethoxy]phenyl}boronic acid 
• 39255-24-8 1-bromo-4-[2-(butoxy)ethoxy]benzene 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 223526-84-9 methyl 5-bromo-2-{[(4-methylphenyl)sulfonyl]amino}benzoate 
• 10503-96-5 1-(2-chloroethoxy)butane 

Downstream Products

• 497850-26-7 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-N-({4-[(4-methyl-4H-1,2,4-triazol-3-yl)methyl]sulfanyl}phenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497850-19-8 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-N-({4-[(1-methyl-1H-1,2,4-triazol-5-yl)methyl]sulfanyl}phenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497850-35-8 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-(4-propyl-4H-1,2,4-triazol-3-ylmethylsulfinyl)phenyl]-2,3-dihydro-1H-benzazepine-4-carboxamide 
• 497852-91-2 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[(1-ethylimidazol-2-yl)methyl]sulfinyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide 
• 497850-94-9 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(2-pyridinylmethyl)sulfinyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide 

Relevant articles and documents

Unusual asymmetric oxidation of sulfide; the diastereoselective oxidation of prochiral sulfide-chiral acid salt with hydrogen peroxide without metal

The sulfide 4 was treated with chiral acid in a mixture of toluene and methyl iso-butylketone to precipitate the salt, which reacted with 30% H 2O2 for 3 weeks at rt. The resulting crystals were collected followed by recrystallizatio

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.

BENZAZEPINE DERIVATIVES, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF

Compounds of the general formula (I): or salts thereof, which exhibit CCR5 antagonism and exert preventive and therapeutic effects against HIV infections: wherein R1 is a 5- to 6-membered aromatic ring which bears a substituent represented by the general formula: R-Z1-X-Z2- (wherein R1 is hydrogen or optionally substituted hydrocarbyl; X is optionally substituted alkylene; and Z1 and Z2 are each a heteroatom) and may be further substituted, with R being optionally bonded to the aromatic ring to form another ring; Y is optionally substituted imino; and R2 and R3 are each optionally substituted aliphatic hydrocarbyl or an optionally substituted hetero-alicyclic group.