Studies on anti-inflammatory agents. VI. Synthesis and pharmacological properties of 2,3-diarylthiophenes.
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)thiop hene (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-alpha production.
Tsuji
K
K
Medicinal Chemistry Research Laboratories, Fujisawa Pharmaceutical Co., Ltd., Osaka, Japan.
Nakamura
K
K
Ogino
T
T
Konishi
N
N
Tojo
T
T
Ochi
T
T
Seki
N
N
Matsuo
M
M
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000494:pharmacology; D000328:Adult; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001169:Arthritis, Experimental / Q000188:drug therapy; D006801:Humans; D006968:Hypersensitivity, Delayed / Q000188:drug therapy; D008297:Male; D051379:Mice; D008811:Mice, Inbred DBA; D051381:Rats; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology*
D000276:Adjuvants, Immunologic; D000893:Anti-Inflammatory Agents; D013876:Thiophenes