Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Anti-inflammatory Agents. VI. Synthesis and Pharmacological Properties of 2, 3-Diarylthiophenes
Kiyoshi TSUJI, Katsuya NAKAMURA, Takashi OGINO, Nobukiyo KONISHI, Takashi TOJO, Takehiro OCHI, Nobuo SEKI, Masaaki MATSUO
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Keywords: anti-inflammatory agent, 2, 3-diarylthiophene, antirheumatic activity, analgesic activity, structure-activity relationship
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1998 Volume 46 Issue 2 Pages 279-286

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Abstract

A series of novel 5-substituted-2, 3-diarylthiophenes has been synthesized and found to be active in the rat adjuvant arthritis (AA) model and/or in the yeast-induced hyperalgesia (Randall-Selitto) assay. Among the compounds synthesized herein, 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiophene (6a) exhibited the most potent activities on AA, collagen-induced arthritis (CIA) and the delayed-type hypersensitivity response to type II collagen. 5-Bromo-2-[4-(methylamino)phenyl]-3-[4-(methylsulfinyl)phenyl]thiophene (38) is also a potent inhibitor of AA, CIA, hyperalgesia and in vitro tumor necrosis factor-α production.

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