497854-65-6

Basic information

• Product Name: 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide
• Synonyms: 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide
• CAS NO: 497854-65-6
• Molecular Weight: 673.732
• Mol File: 497854-65-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide(497854-65-6)
• EPA Substance Registry System: 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(pyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide(497854-65-6)

Safety Data

• Hazardous Substances Data: 497854-65-6(Hazardous Substances Data)

Upstream product

• 497851-60-2 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 313750-60-6 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 22162-15-8 (2-methyl-4-nitro-phenyl)methanol 
• 99-51-4 4-nitro-o-xylene 
• 497854-64-5 (4-amino-2-methylphenyl)(pyridin-2-yl)methanol 
• 497851-72-6 7-[4-(2-butoxyethoxy)phenyl]-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 72005-84-6 2-methyl-4-nitro-benzaldehyde 
• 22162-14-7 1-(bromomethyl)-2-methyl-4-nitrobenzene 

Downstream Products

• 497849-03-3 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methylphenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497851-48-6 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methylphenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 

Relevant articles and documents

Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety

In order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC 50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.