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

共 49 条

[21] Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C-H Bond Activation [J].

Kim, Ji Young ;

Park, Sae Hume ;

Ryu, Jaeyune ;

Hwan, Seung Cho ;

Kim, Seok Hwan ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9110-9113

[22] Formal SN-Type Reactions in Rhodium(III)-Catalyzed C-H Bond Activation [J].

Kuhl, Nadine ;

Schroeder, Nils ;

Glorius, Frank .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1443-1460

[23] Oscarellin, an Anthranilic Acid Derivative from a Philippine Sponge, Oscarella stillans, as an Inhibitor of Inflammatory Cytokines in Macrophages [J].

Kwon, Ii-Seal ;

Kwak, Jong Hwan ;

Pyo, Suhkneung ;

Lee, Hee-Weon ;

Kim, AeRyon ;

Schmitz, Francis J. .

JOURNAL OF NATURAL PRODUCTS, 2017, 80 (01) :149-155

[24] Direct C-H Amidation of Benzoic Acids to Introduce meta- and para-Amino Groups by Tandem Decarboxylation [J].

Lee, Donggun ;

Chang, Sukbok .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (14) :5364-5368

[25] The discovery of anthranilic acid-based MMP inhibitors. Part 1: SAR of the 3-position [J].

Levin, JI ;

Du, MT ;

DiJoseph, JF ;

Killar, LM ;

Sung, A ;

Walter, T ;

Sharr, MA ;

Roth, CE ;

Moy, FJ ;

Powers, R ;

Jin, GX ;

Cowling, R ;

Skotnicki, JS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (02) :235-238

[26] Pd-Catalyzed Intermolecular ortho-C-H Amidation of Anilides by N-Nosyloxycarbamate [J].

Ng, Ka-Ho ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) :12862-12864

[27] Comparative Catalytic Activity of Group 9 [Cp*MIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents [J].

Park, Juhyeon ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14103-14107

[28] Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating Reagent [J].

Park, Yoonsu ;

Park, Kyung Tae ;

Kim, Jeung Gon ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (13) :4534-4542

[29] ANTIFUNGAL ACTIVITY OF SOME N-SUBSTITUTED ANTHRANILIC ACID-DERIVATIVES [J].

RAMANUJAM, P ;

ASTHANA, JG .

PLANTA MEDICA, 1974, 25 (01) :43-46

[30]

Roberts L.J.I.M., 2001, PHARM BASIS THERAPEU, P687

← 1 2 3 4 5 →