Anti-Inflammatory Activity of para-Substituted N-Benzenesulfonyl Derivatives of Anthranilic Acid

• Published in: Journal of pharmaceutical sciences 1974-04, Vol.63 (4), p.615-617
• Main Authors: Borne, Ronald F., Peden, Richard L., Waters, I.W., Weiner, Myra, Jordan, Robert, Coats, Eugene A.
• Format: Article
• Language: English
• Subjects: Animals; Anthranilic acid; Anthranilic acid, para-substituted N-benzenesulfonyl derivatives—synthesized and screened for anti-inflammatory activity; Anti-inflammatory activity-para-substituted. N-benzenesulfonyl derivatives of anthranilic acid; Anti-inflammatory activity—para-substituted. N-benzenesulfonyl derivatives of anthranilic acid, synthesis and screening; Anti-Inflammatory Agents - pharmacology; Benzene Derivatives - chemical synthesis; Benzene Derivatives - pharmacology; Benzene Derivatives - therapeutic use; Benzene Derivatives - toxicity; Carrageenan; Edema - chemically induced; Edema - drug therapy; Erythrocytes - drug effects; Humans; In Vitro Techniques; Lethal Dose 50; ortho-Aminobenzoates - chemical synthesis; ortho-Aminobenzoates - pharmacology; ortho-Aminobenzoates - therapeutic use; ortho-Aminobenzoates - toxicity; para-substituted N-benzenesulfonyl derivatives-synthesized and screened for anti-inflammatory activity; Rats; Structure-Activity Relationship; Structure-activity relationships-para-substituted N-benzenesulfonyl derivatives of anthranilic acid; Sulfonamides - chemical synthesis; Sulfonamides - pharmacology; Sulfonamides - therapeutic use; Sulfonamides - toxicity; synthesis and screening
• ISSN: 0022-3549; 1520-6017
• DOI: 10.1002/jps.2600630428

Several para-substituted N-benzenesulfonyl derivatives of anthranilic acid were prepared and evaluated for anti-inflammatory activity using erythrocyte membrane stabilization and carrageenin-induced rat paw edema assays. N-p-Bromobenzenesulfonylanthranilic acid possessed greater activity than phenylbutazone in both assays. Quantitative structure-activity correlations employing the Hansch method were unsuccessful in the erythrocyte membrane stabilization assay. However, correlations were obtained in the rat paw edema assay, and it appears that the activity of these derivatives depends solely on the lipophilic character of the substituents on the benzenesulfonyl ring.