title: A stereo configuration-activity study of 3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(2H)-ones as potency inhibitors of HIV-1 variants.
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.
authors.affiliation: Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China. Xiaoweiwang@bjmu.edu.cn Jyliu@bjmu.edu.cn.
authors.forename: Shaotong
authors.initials: S
authors.lastname: Wu
authors.forename: Qianqian
authors.initials: Q
authors.lastname: Yin
authors.forename: Liang
authors.initials: L
authors.lastname: Zhao
authors.forename: Ningning
authors.initials: N
authors.lastname: Fan
authors.forename: Xiaowan
authors.initials: X
authors.lastname: Tang
authors.forename: Jianxiong
authors.initials: J
authors.lastname: Zhao
authors.forename: Tao
authors.initials: T
authors.lastname: Sheng
authors.forename: Ying
authors.initials: Y
authors.lastname: Guo
authors.forename: Chao
authors.initials: C
authors.lastname: Tian
authors.forename: Zhili
authors.initials: Z
authors.lastname: Zhang
authors.forename: Weisi
authors.initials: W
authors.lastname: Xu
authors.forename: Zhenming
authors.initials: Z
authors.lastname: Liu
authors.forename: Shibo
authors.initials: S
authors.lastname: Jiang
authors.forename: Liying
authors.initials: L
authors.lastname: Ma
authors.forename: Junyi
authors.initials: J
authors.lastname: Liu
authors.forename: Xiaowei
authors.initials: X
authors.lastname: Wang
mesh_terms: D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D014644:Genetic Variation / Q000187:drug effects; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors* / Q000235:genetics; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology / Q000235:genetics*; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C000610518:3-iodo-4-(2-methylcyclohexyloxy)-6-phenethylpyridin-2(1H)-one; D011728:Pyridones; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase