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Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors 期刊论文

编号：

0b5bdfed-64eb-4f8e-ac2a-27965ade221d
作者：

Gu, ShuangXi^[1] Li, ZhiMing^[1] Ma, XiaoDong^[1] Yang, ShiQiong^[1] He, QiuQin^[1] Chen, FenEr^[1,2] De Clercq, Erik^[3] Balzarini, Jan^[3] Pannecouque, Christophe^[3]
语种：

English
期刊：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY ISSN：0223-5234 2012 年 53 卷 (229 - 234) ; JUL
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关键词：

HIV-1 NNRTIs Diarylpyrimidines Chiral resolution Absolute configuration Molecular docking
摘要：

(+)-3a and (-)-3a were successfully separated from racemate (+/-)-3a by the chiral technique of supercritical fluid chromatography (SCF) with enantiomeric excess (ee%) >99% and purity >99%, and assigned for their absolute configuration as R and S, respectively, by the experimental electronic circular dichroism (ECD) spectrum and simulated ECD spectra calculated by time-dependent density functional theory (TDDFT) calculations. (+)-(R)-3a displayed excellent activity with an EC50 of 5.3 nM against wild-type HIV-1, which was 12-fold more potent than (-)-(S)-3a. However, (-)-(S)-3a showed higher potency than (+)-(R)-3a against the double HIV-1 RT mutant (K103N + Y181C) as well as HIV-2 strain ROD. The possible reason for the difference of (R)- and (S)-3a in anti-HIV-1 activity was interpreted by molecular docking. (C) 2012 Elsevier Masson SAS. All rights reserved.
推荐引用方式
GB/T 7714：

Gu Shuang-Xi,Li Zhi-Ming,Ma Xiao-Dong, et al. Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors [J].EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2012,53:229-234.
APA：

Gu Shuang-Xi,Li Zhi-Ming,Ma Xiao-Dong,Yang Shi-Qiong,&Pannecouque Christophe.(2012).Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors .EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,53:229-234.
MLA：

Gu Shuang-Xi, et al. "Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors" .EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 53(2012):229-234.

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