Discovery and structure-activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors

被引：48

作者：

Cheng, Ming-Fu ^{[1
]}

Hung, Ming-Shiu ^{[1
]}

Song, Jen-Shin ^{[1
]}

Lin, Shu-Yu ^{[1
]}

Liao, Fang-Yu ^{[1
]}

Wu, Mine-Hsine ^{[1
]}

Hsiao, Wenchi ^{[1
]}

Hsieh, Chia-Ling ^{[1
]}

Wu, Jian-Sung ^{[1
]}

Chao, Yu-Sheng ^{[1
]}

Shih, Chuan ^{[1
]}

Wu, Su-Ying ^{[1
]}

Ueng, Shau-Hua ^{[1
]}

机构：

[1] Natl Hlth Res Inst, Inst Biotechnol & Pharmaceut Res, Zhunan 35053, Miaoli County, Taiwan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 15期

关键词：

Sulfonylhydrazide; Indoleamine 2,3-dioxygenase; Structure-activity relationship; Molecular docking; CANCER-IMMUNOTHERAPY; DERIVATIVES; INDOLEAMINE-2,3-DIOXYGENASE; BLOCKADE; TARGET; PD-1;

D O I：

10.1016/j.bmcl.2014.05.084

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel class of phenyl benzenesulfonylhydrazides has been identified as potent inhibitors of indoleamine 2,3-dioxygenase (IDO), and their structure-activity relationship was explored. Coupling reactions between various benzenesulfonyl chlorides and phenylhydrazides were utilized to synthesize the sulfonylhydrazides bearing various substituents. Compound 3i exhibited 61 nM of IC50 in enzymatic assay and 172 nM of EC50 in the HeLa cell. The computational study of 3i suggested that the major interactions between 3i and IDO protein are the coordination of sulfone and heme iron, the hydrogen bonding and hydrophobic interactions between 3i and IDO. This novel class of IDO inhibitor provides a new direction to discover effective anti-cancer agents. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3403 / 3406

页数：4

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