A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants

Shaotong Wu; Qianqian Yin; Liang Zhao; Ningning Fan; Xiaowan Tang; Jianxiong Zhao; Tao Sheng; Ying Guo; Chao Tian; Zhili Zhang; Weisi Xu; Zhenming Liu; Shibo Jiang; Liying Ma; Junyi Liu; Xiaowei Wang

doi:10.1039/C5OB02154E

A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants†

Shaotong Wu,‡^a Qianqian Yin,‡^b Liang Zhao,^c Ningning Fan,^a Xiaowan Tang,^a Jianxiong Zhao,^a Tao Sheng,^a Ying Guo,^a Chao Tian,^a Zhili Zhang,^a Weisi Xu,^b Zhenming Liu,^c Shibo Jiang,^d Liying Ma,*^b Junyi Liu*^ac and Xiaowei Wang*^a

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* Corresponding authors

^a Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
E-mail: Xiaoweiwang@bjmu.edu.cn, Jyliu@bjmu.edu.cn

^b National Center for AIDS/STD Control and Prevention (NCAIDS), Chinese Center for Disease Control and Prevention, Beijing 102206, China
E-mail: mal@chinaaids.cn

^c State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

^d Laboratory of Medical Molecular Virology of Ministries of Education and Health, Fudan University, Shanghai 200032, China

Abstract

3-Iodo-4-(2′-methylcyclohexyloxy)-6-phenethylpyridin-2(1H)-ones, as effective non-nucleoside reverse transcriptase inhibitors, were synthesized and resolved with different configurations. Biological results revealed that the trans-racemate 2b exhibited more potent activity than the cis-isomers. Noticeably, the trans-(S,S)-enantiomer 2e turned out to be significantly more potent than its counterpart enantiomer 2d against wild-type and double-mutant strains with high selectivity indexes.

Organic & Biomolecular Chemistry

A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants†

Abstract

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A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants

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