Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

被引：12

作者：

Kwon, Tae Hoon ^{[1
,2
]}

Yoon, Ik Hwan ^{[1
,2
]}

Shin, Ji-Sun ^{[2
]}

Lee, Young Hun ^{[1
,2
]}

Kwon, Bong Jin ^{[1
,2
]}

Lee, Kyung-Tae ^{[1
,2
]}

Lee, Yong Sup ^{[1
,2
]}

机构：

[1] Kyung Hee Univ, Dept Life & Nanopharmaceut Sci, Seoul 130701, South Korea

[2] Kyung Hee Univ, Coll Pharm, Dept Pharm, Seoul 130701, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 09期

基金：

新加坡国家研究基金会;

关键词：

Arvelexin; Indole-3-acetonitrile; Nitric oxide; Prostaglandin E-2; Anti-inflammatory; NF-KAPPA-B; PHYTOALEXINS; ROOTS; PHYTOANTICIPINS; EXPRESSION; RAPA;

D O I：

10.1016/j.bmcl.2013.02.114

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE(2) productions and was less cytotoxic than arvelexin on macrophage cells. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2571 / 2574

页数：4

共 16 条

[1]

Bang MH, 2008, J KOREAN SOC APPL BI, V51, P65

[2] Chronic inflammation:: importance of NOD2 and NALP3 in interleukin-1β generation [J].

Ferrero-Miliani, L. ;

Nielsen, O. H. ;

Andersen, P. S. ;

Girardin, S. E. .

CLINICAL AND EXPERIMENTAL IMMUNOLOGY, 2007, 147 (02) :227-235

[3] Cyclooxygenase-2 - 10 years later [J].

Hinz, B ;

Brune, K .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2002, 300 (02) :367-375

[4] CHANGES IN THE INCIDENCE AND PREVALENCE OF RHEUMATOID-ARTHRITIS IN ENGLAND AND WALES, 1970-1982 [J].

HOCHBERG, MC .

SEMINARS IN ARTHRITIS AND RHEUMATISM, 1990, 19 (05) :294-302

[5] Isoliquiritigenin isolated from the roots of Glycyrrhiza uralensis inhibits LPS-induced NOS and COX-2 expression via the attenuation of NF-κB in RAW 264.7 macrophages [J].

Kim, Ji-Yeon ;

Park, Seung Jae ;

Yun, Kyung-Jin ;

Cho, Young-Wuk ;

Park, Hee-Juhn ;

Lee, Kyung-Tae .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2008, 584 (01) :175-184

[6] Dextran sulfate sodium and 2,4,6-trinitrobenzene sulfonic acid induce lipid peroxidation by the proliferation of intestinal gram-negative bacteria in mice [J].

Lee, In-Ah ;

Bae, Eun-Ah ;

Hyun, Yang-Jin ;

Kim, Dong-Hyun .

JOURNAL OF INFLAMMATION-LONDON, 2010, 7

[7] Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study [J].

Mor, M ;

Rivara, S ;

Silva, C ;

Bordi, F ;

Plazzi, PV ;

Spadoni, G ;

Diamantini, G ;

Balsamini, C ;

Tarzia, G ;

Fraschini, F ;

Lucini, V ;

Nonno, R ;

Stankov, BM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (20) :3831-3844

[8] Metabolic Changes in Roots of the Oilseed Canola Infected with the Biotroph Plasmodiophora brassicae: Phytoalexins and Phytoanticipins [J].

Pedras, M. Soledade C. ;

Zheng, Qing-An ;

Strelkov, Stephen .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (21) :9949-9961

[9] Phytoalexins and phytoanticipins from the wild crucifers Thellungiella halophila and Arabidopsis thaliana:: Rapalexin A, wasalexins and camalexin [J].

Pedras, M. Soledade C. ;

Adio, Adewale M. .

PHYTOCHEMISTRY, 2008, 69 (04) :889-893

[10] Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans:: structures, syntheses and antifungal activity [J].

Pedras, MSC ;

Chumala, PB ;

Suchy, M .

PHYTOCHEMISTRY, 2003, 64 (05) :949-956

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