title: Antiinflammatory 4,5-diarylpyrroles: synthesis and QSAR.
abstract: 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.
authors.affiliation: Du Pont Merck Pharmaceutical Company, Wilmington, Delaware 19880-0353.
authors.forename: W W
authors.initials: WW
authors.lastname: Wilkerson
authors.forename: W
authors.initials: W
authors.lastname: Galbraith
authors.forename: K
authors.initials: K
authors.lastname: Gans-Brangs
authors.forename: M
authors.initials: M
authors.lastname: Grubb
authors.forename: W E
authors.initials: WE
authors.lastname: Hewes
authors.forename: B
authors.initials: B
authors.lastname: Jaffee
authors.forename: J P
authors.initials: JP
authors.lastname: Kenney
authors.forename: J
authors.initials: J
authors.lastname: Kerr
authors.forename: N
authors.initials: N
authors.lastname: Wong
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000627:therapeutic use / Q000633:toxicity; D001169:Arthritis, Experimental / Q000188:drug therapy; D004195:Disease Models, Animal; D004361:Drug Tolerance; D008297:Male; D011758:Pyrroles / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000627:therapeutic use / Q000633:toxicity; D051381:Rats; D017207:Rats, Sprague-Dawley; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D011758:Pyrroles