279262-28-1

Basic information

• Product Name: Boronic acid, [4-(2-butoxyethoxy)phenyl]-
• CAS NO: 279262-28-1
• Molecular Formula: C12H19BO4
• Molecular Weight: 238.091
• Mol File: 279262-28-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Boronic acid, [4-(2-butoxyethoxy)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, [4-(2-butoxyethoxy)phenyl]-(279262-28-1)
• EPA Substance Registry System: Boronic acid, [4-(2-butoxyethoxy)phenyl]-(279262-28-1)

Safety Data

• Hazardous Substances Data: 279262-28-1(Hazardous Substances Data)

Upstream product

• 10503-96-5 1-(2-chloroethoxy)butane 
• 39255-24-8 1-bromo-4-[2-(butoxy)ethoxy]benzene 

Downstream Products

• 313736-28-6 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 313740-83-9 7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide 

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.