4-Hydroxy-3-(naphthalen-1-ylmethyl)thiophen-2(5H)-one as inhibitors of tyrosyl-tRNA synthase: Synthesis, molecular docking and antibacterial evaluation

被引：2
|
作者：
Sun, Juan [1 ]
Liu, Jia-Jia [1 ]
Zhou, Wei [2 ]
Guo, Feng-Jiao [2 ]
Wang, Xin-Yi [2 ]
Zhu, Hai-Liang [1 ,2 ]
机构：
[1] Nanjing Univ, State Key Lab Pharmaceut Biotechnol, Nanjing 210093, Jiangsu, Peoples R China
[2] Shandong Univ Technol, Sch Life Sci, Zibo 255049, Shandong, Peoples R China
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2014年 / 1056卷
关键词：
Thiophenone; Antibacterial; Tyrosyl-tRNA synthase; Structure-activity relationship; Molecular docking; POTENT; THIOLACTOMYCIN; SYNTHETASE; ANALOGS; FACILE;
D O I：
10.1016/j.molstruc.2013.10.032
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A series of novel 4-hydroxy-3-(naphthalen-1-ylmethyl)thiophen-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 4-(naphthalen-1-ylmethyl)-5-oxo-2,5-dihydrothiophen-3-yl-2-(4-hydroxyphenyl)acetate (29) was the most potent. The binding model and structure-activity relationship indicate that replacement of phenyl acetate in the side chain of 29 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 29 is the most potent agent against Staphylococcus aureus ATCC 25923 with MIC50 value of 0.21 mu g/mL. (C)2013 Elsevier B.V. All rights reserved.
引用
收藏
页码：104 / 109
页数：6
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