Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

Abstract

A series of novel 2-(thiazol-2-yl)-octahydropyrrolo [3,4-c]pyrroles was synthesized by reaction of octahydropyrrolo [3,4-c]pyrrole N-benzoylthiourea derivatives and -haloketones in subcritical water at 130 C in 75-91% yield. Both the thiourea intermediates and the end products were synthesized in subcritical water, which proved a suitable green alternative to acetone by delivering the desired compounds in much shorter reaction times and practically the same yields. The antimicrobial activity of the compounds was determined against five bacterial strains and three fungal strains, and MIC values of 15.62-250 g/mL were observed. Moreover, the compounds exhibited antimycobacterial activity against M. tuberculosis H37Rv with MIC values of 7.81-62.5 g/mL.