Antiinflammatory 4,5-Diarylpyrroles: Synthesis and QSAR

A series of 2-substituted- and 2,3-disubstituted-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H- pyrroles was synthesized and found to be active in the rat adjuvant arthritis model of inflammation. The most active compounds were the 2-halo derivatives in the order of chloro > bromo > iodo....

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Veröffentlicht in:Journal of medicinal chemistry 1994-04, Vol.37 (7), p.988-998
Hauptverfasser: Wilkerson, Wendell W, Galbraith, William, Gans-Brangs, Kathleen, Grubb, Mary, Hewes, Walter E, Jaffee, Bruce, Kenney, J. P, Kerr, Janet, Wong, Nancy
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Sprache:eng
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Zusammenfassung:A series of 2-substituted- and 2,3-disubstituted-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H- pyrroles was synthesized and found to be active in the rat adjuvant arthritis model of inflammation. The most active compounds were the 2-halo derivatives in the order of chloro > bromo > iodo. The same pattern of activity was observed for the 2,3-dihalopyrroles. Quantitative structure-activity relationship studies suggested that the activity could be correlated with the molar refractivity and the inductive field effect of the 2-substituent and the lipophilicity of the 3-substituent.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00033a017