Green synthesis of new sulfanyl derivatives of ampyrone and prediction of their anti-inflammatory activity

Abstract

A selective method was developed for the synthesis of acyclic sulfanyl derivatives of ampyrone by thiomethylation reaction of 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one with formaldehyde and thiols in aqueous medium under various conditions (room temperature, 80°C, ultrasonication or microwave irradiation). A series of the synthesized sulfanyl derivatives of ampyrone were characterized with regard to their anti-inflammatory activity by molecular docking method using the AutoDock 4.2 and AutoDock Vina software. The steric complementarity with the active sites of cyclooxygenase isoforms (COX-1 and COX-2) was explored.