Synthesis and anti-inflammatory activity evaluation of some sulfonamide and amidine derivatives of 4-aryl-3-(2 or 4-picolyl)-2-imino-4-thiazolines

摘要

Condensation of 2- and 4-picolylaminehydrochloride 2a,b with (un) substituted phenacylthiocyanate 1a-d gives 4-aryl-3-(2- or 4-picolyl)-2-imino-4-thiazolines 3a-h in moderate yields. Sulfonamide derivatives 4a-h have been synthesized by condensation of 4-aryl-3-(2- or 4-picolyl)-2-imino-4-thiazolines 3a-h with methanesulfonylchloride in good yields. Condensation of 2-cyanopyridine with thiazolines 3a, 3e and of 4-cyanopyridine with 3a, c, e and h gives amidine derivatives 5a, b and 6a-d respectively. Thiazoline derivatives 3a-h, sulfonamide derivatives 4a-h and amidine derivatives 5a, b; 6a-d are characterized by IR, ~1H NMR, GC-MS spectral data and elemental analysis. Anti-inflammatory activity evaluation of 3a-h, 4a-d, g-h, 5a,b and 6a-c using carageenan induced paw oedema assay at 50 mg/kg p.o. has been carried out and compound 6a exhibited anti-inflammatory activity comparable to standard drug ibuprofen.