Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: evaluation of antibacterial and antifungal activities along with docking studies

Abstract

A sequential multicomponent synthesis of highly substituted pyrrole-3-carboxaldehydes has been developed under metal-free conditions. This one-pot protocol involves proline-catalyzed direct chemoselective Mannich reaction-cyclization between 1,4-ketoaldehyde and in situ generated Ar/HetAr-imines followed by aerobic oxidative-aromatization at room temperature. A series of fully substituted pyrrole-3-carboxaldehydes and other diverse fused heterocycles have been synthesized. These compounds were tested for in vitro antibacterial and antifungal activities, and the selected ones display significant activity against the tested bacterial strains with a MIC value of 16 μg mL⁻¹, which is close to that of the standard drug chloramphenicol. The bioactivity outcome was further analyzed using docking studies.