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  • Inhibitors of HIV-1 attachment. Part 7: indole-7-carboxamides as potent and orally bioavailable antiviral agents.

Inhibitors of HIV-1 attachment. Part 7: indole-7-carboxamides as potent and orally bioavailable antiviral agents.

Bioorganic & medicinal chemistry letters (2012-12-04)
Kap-Sun Yeung, Zhilei Qiu, Quifen Xue, Haiquan Fang, Zheng Yang, Lisa Zadjura, Celia J D'Arienzo, Betsy J Eggers, Keith Riccardi, Pei-Yong Shi, Yi-Fei Gong, Marc R Browning, Qi Gao, Steven Hansel, Kenneth Santone, Ping-Fang Lin, Nicholas A Meanwell, John F Kadow
ABSTRACT

A series of substituted carboxamides at the indole C7 position of the previously described 4-fluoro-substituted indole HIV-1 attachment inhibitor 1 was synthesized and the SAR delineated. Heteroaryl carboxamide inhibitors that exhibited pM potency in the primary cell-based assay against a pseudotype virus expressing a JRFL envelope were identified. The simple methyl amide analog 4 displayed a promising in vitro profile, with its favorable HLM stability and membrane permeability translating into favorable pharmacokinetic properties in preclinical species.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Indole, ≥99%
Supelco
Indole solution, 2000 μg/mL in methanol, certified reference material
Supelco
Indole, analytical standard
Sigma-Aldrich
Indole, ≥99%, FG