Design, Synthesis, and X-ray Crystallographic Analysis of a Novel Class of HIV-1 Protease Inhibitors
Journal of Medicinal Chemistry2011Vol. 54(20), pp. 7176–7183
Citations Over TimeTop 14% of 2011 papers
Ashit K. Ganguly, S. Alluri, D. Caroccia, D. Biswas, Chih‐Hung Wang, Eun‐Hee Kang, Yong Zhang, Andrew T. McPhail, Steven S. Carroll, Christine Burlein, Vandna Munshi, Peter Orth, Corey Strickland
Abstract
In the present paper, design, synthesis, X-ray crystallographic analysis, and HIV-1 protease inhibitory activities of a novel class of compounds are disclosed. Compounds 28-30, 32, 35, and 40 were synthesized and found to be inhibitors of the HIV-1 protease. The crucial step in their synthesis involved an unusual endo radical cyclization process. Absolute stereochemistry of the three asymmetric centers in the above compounds have been established to be (4S,2'R,3'S) for optimal potency. X-ray crystallographic analysis has been used to determine the binding mode of the inhibitors to the HIV-1 protease.
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