Base promoted synthesis of novel indole-dithiocarbamate compounds as potential anti-inflammatory therapeutic agents for treatment of acute lung injury

被引：48

作者：

Song, Zengqiang ^{[1
]}

Zhou, Yan ^{[1
]}

Zhang, Wenxin ^{[1
]}

Zhan, Lingling ^{[2
]}

Yu, Yuanzu ^{[1
]}

Chen, Yuehui ^{[2
]}

Jia, Wenjing ^{[1
]}

Liu, Zhiguo ^{[1
]}

Qian, Jianchang ^{[1
]}

Zhang, Yali ^{[1
]}

Li, Chenglong ^{[1
]}

Liang, Guang ^{[1
]}

机构：

[1] Wenzhou Med Univ, Sch Pharmaceut Sci, Chem Biol Res Ctr, Wenzhou 325035, Zhejiang, Peoples R China

[2] Wenzhou Med Univ, Affiliated Hosp 1, Wenzhou 325035, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2019年 / 171卷

基金：

中国国家自然科学基金;

关键词：

N-S bond formation; lndole-dithiocarbamates; Anti-inflammation; ALI; DERIVATIVES; SULFENYLATION; GROWTH; POLYMERIZATION; INTERLEUKIN-6; PATHOGENESIS; INHIBITORS; CHEMISTRY; PATHWAY;

D O I：

10.1016/j.ejmech.2019.03.022

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An efficient protocol for highly chemoselective introduction of dithiocarbamate groups to nitrogen position of indoles with bis(dialkylaminethiocarbonyl)disulfides was achieved by employing t-BuOK as a promoter. Based on this methodology, twenty nine novel indole-dithiocarbamate compounds were prepared in moderate to excellent yields at room temperature. All compounds were evaluated for their anti-inflammatory activity. Most of the compounds exhibited high potency on inhibiting the releasing of tumor necrosis factor alpha (TNF-alpha) and interleukin-6 (IL-6). Four of them were found to suppress in vitro cytokine production in a dose-dependent manner with IC50 values in the nanomolar range. Additionally, 3-methyl-1H-indo1-1-yl dimethylcarbamodithioate (3o) effectively ameliorated histopathological changes of lung tissues and attenuated lipopolysaccharides (LPS)-induced acute lung injury (ALI) in vivo. These data suggest that the new indole-dithiocarbamate derivatives could be particularly useful for further pharmaceutical development for the treatment of ALI. (C) 2019 Elsevier Masson SAS. All rights reserved.

引用

页码：54 / 65

页数：12

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