Discovery of 4-Benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2- (R)-methylpiperazine (BMS-378806): A Novel HIV-1 Attachment Inhibitor That Interferes with CD4-gp120 Interactions
Journal of Medicinal Chemistry2003Vol. 46(20), pp. 4236–4239
Citations Over TimeTop 10% of 2003 papers
Tao Wang, Zhongxing Zhang, Owen B. Wallace, Milind Deshpande, Haiquan Fang, Zheng Yang, Lisa Zadjura, Donald L. Tweedie, Stella Huang, Fang Zhao, Sunanda A. Ranadive, Brett S. Robinson, Yi-Fei Gong, Keith Ricarrdi, Timothy Spicer, Carol Deminie, Ronald E. Rose, Hwei-Gene Heidi Wang, Wade Blair, Pei‐Yong Shi, Pin-fang Lin, Richard J. Colonno, Nicholas A. Meanwell
Abstract
Indole derivative 1 interferes with the interaction of the HIV surface protein gp120 with the host cell receptor CD4. The 4-fluoro derivative 2 exhibited markedly enhanced potency and was bioavailable in the rat, dog, and cynomolgus monkey when administered orally as a solution formulation. However, aqueous suspensions of 2 were poorly bioavailable, indicative of dissolution-limited absorption. The 7-azaindole derivative 3, BMS-378806, exhibited improved pharmaceutical properties while retaining the HIV-1 inhibitory profile of 2.
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