Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents

• Published in: Journal of medicinal chemistry Vol. 27; no. 12; pp. 1565 - 1570
• Main Authors: Maxwell, James R, Wasdahl, Dan A, Wolfson, Alan C, Stenberg, Virgil I
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.12.1984
• Subjects: Acetates - chemical synthesis; Acetates - pharmacology; Animals; Anti-Inflammatory Agents - chemical synthesis; Arthus Reaction; Azoles - chemical synthesis; Biological Assay; Chemistry; Edema - drug therapy; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Indicators and Reagents; Magnetic Resonance Spectroscopy; Organic chemistry; Preparations and properties; Rats; Spectrophotometry, Infrared; Structure-Activity Relationship; Superoxides - metabolism; Tetrazoles - chemical synthesis; Tetrazoles - pharmacology; Triazoles - chemical synthesis; Triazoles - pharmacology; Non steroidal antiinflammatory agent; Five membered ring; Nitrogen heterocycle; Phenols; Mercaptoacid; Diphenols; In vitro; Radical scavenger; Biological activity; Organic sulfide
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00378a007

A series of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids were synthesized and tested in vitro for superoxide scavenging activity, in vivo in the carrageenan-induced rat paw edema assay, and in the reverse passive Arthus reaction. The hydroxy-substituted compounds were effective as in vitro scavengers of superoxide but were not effective as in vivo antiinflammatory agents.