Design, synthesis and evaluation of novel molecules with a diphenyl ether nucleus as potential antitubercular agents

被引：19
|
作者：
Yang, Yinghong [1 ,2 ]
Wang, Zhenling [2 ]
Yang, Jianzhong [2 ]
Yang, Tao [2 ]
Pi, Weiyi [2 ]
Ang, Wei [3 ]
Lin, Yanni [2 ]
Liu, Yuanyuan [2 ]
Li, Zicheng [1 ]
Luo, Youfu [2 ]
Wei, Yuquan [2 ]
机构：
[1] Sichuan Univ, Dept Pharmaceut & Bioengn, Sch Chem Engn, Chengdu 610065, Sichuan, Peoples R China
[2] Sichuan Univ, State Key Lab Biotherapy, W China Hosp, W China Med Sch, Chengdu 610041, Sichuan, Peoples R China
[3] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, W China Med Sch, Chengdu 610041, Sichuan, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 02期
关键词：
Diphenyl ether nucleus; Antituberculosis; H(37)Rv; BCG murine model; ANTIBACTERIAL AGENT; TRICLOSAN; IDENTIFICATION; INHIBITORS; DOCKING;
D O I：
10.1016/j.bmcl.2011.12.022
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of compounds with a diphenyl ether nucleus were synthesized by incorporating various amines into the diphenyl ether scaffold with an amide bond. Their antitubercular activities were evaluated against Mycobacterium tuberculosis H(37)Rv by a microdilution method, with MIC values ranging from 4 to 64 mu g/mL. Through structure-activity relationship studies, the two chlorine atoms at 3 and 4 positions in the phenyl ring of R-2 group were found to play a significant role in the antitubercular activity. The most potent compound 6c showed an MIC value of 4 mu g/mL and a good safety profile in HepG2 cell line by the MTT assay. Compound 6c was further found to be effective in a murine model of BCG infection, providing a good lead for subsequent optimization. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：954 / 957
页数：4
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