Synthesis and anti-inflammatory evaluation of N-sulfonyl anthranilic acids via Ir(III)-catalyzed C-H amidation of benzoic acids

被引：16

作者：

Han, Sang Hoon ^{[1
]}

Suh, Hyo Sun ^{[1
]}

Jo, Hyeim ^{[1
]}

Oh, Yongguk ^{[1
]}

Mishra, Neeraj Kumar ^{[1
]}

Han, Sangil ^{[1
]}

Kim, Hyung Sik ^{[1
]}

Jung, Young Hoon ^{[1
,2
]}

Lee, Byung Mu ^{[1
]}

Kim, In Su ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Suwon 16419, South Korea

[2] GBSA, Bioctr, Suwon 16229, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 10期

关键词：

Anthranilic acids; Anti-inflammatory; Benzoic acids; Sulfonyl azides; Iridium; AMINATION; AZIDES; DERIVATIVES; DISCOVERY; ARENES; BONDS; FUNCTIONALIZATIONS; INFLAMMATION; MACROPHAGES; SUPPRESSION;

D O I：

10.1016/j.bmcl.2017.03.072

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The iridium(III)-catalyzed ortho-C-H amidation of benzoic acids with sulfonyl azides is described. These transformations allow the facile generation of N-sulfonyl anthranilic acids, which are known as crucial scaffolds found in biologically active molecules. In addition, all synthetic products were evaluated for in vitro anti-inflammatory activity against interleukin-1 beta (IL-1 beta) and cyclooxygenase-2 (COX-2) with lipopolysaccharide (LPS)-induced RAW264.7 cells. Notably, compounds 4c and 4d, generated from p-OMe- and p-Br-sulfonyl azides, were found to display potent anti-inflammatory property stronger than that of well-known NSAIDs ibuprofen. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2129 / 2134

页数：6

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