Preparation, antiarthritic and analgesic activity of 4,5-diaryl-2-(substituted thio)-1H-imidazoles and their sulfoxides and sulfones

A series of 4,5-diaryl-2-(substituted thio)-1H-imidazoles was synthesized and evaluated as antiinflammatory and analgesic agents in the rat adjuvant induced arthritis assay and the mouse phenyl-p-benzoquinone writhing (PQW) assay. Several analogues were found to be more potent than phenylbutazone an...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1985-09, Vol.28 (9), p.1188-1194
Main Authors: Sharpe, Thomas R, Cherkofsky, Saul C, Hewes, Walter E, Smith, Dewey H, Gregory, Walter A, Haber, Stephen B, Leadbetter, Michael R, Whitney, Joel G
Format: Article
Language:English
Subjects:
Analgesia
Animals
Anti-Inflammatory Agents
Arthritis - drug therapy
Arthritis, Experimental - drug therapy
Chemical Phenomena
Chemistry
Exact sciences and technology
Female
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imidazoles - chemical synthesis
Imidazoles - therapeutic use
Indomethacin - therapeutic use
Male
Mice
Organic chemistry
Phenylbutazone - therapeutic use
Preparations and properties
Rats
Rats, Inbred Lew
Structure-Activity Relationship
Sulfones
Sulfoxides
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Summary:A series of 4,5-diaryl-2-(substituted thio)-1H-imidazoles was synthesized and evaluated as antiinflammatory and analgesic agents in the rat adjuvant induced arthritis assay and the mouse phenyl-p-benzoquinone writhing (PQW) assay. Several analogues were found to be more potent than phenylbutazone and indomethacin. Structure-activity relationships are discussed. One of the compounds, 4,5-bis(4-fluorophenyl)-2-[(1,1,2,2-tetrafluoroethyl)-sulfonyl]-1H- imidazole (8d, tiflamizole), was found to be 8 times as potent as indomethacin in the rat adjuvant induced arthritis assay and is presently undergoing clinical trial as an antiarthritic drug.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00147a011