Synthesis, Molecular Docking Studies and Antimicrobial Activity of Mannich Bases of Thiazolidine-2,4-Diones

Abstract

The aim of study was to synthesize a new series of mannich bases of thiazolidine-2,4-diones. A new series of mannich bases of thiazolidine-2,4-diones have been synthesized by mannich base reaction between 5-substituted thiazolidine-2,4-dione, acetanilide and aromatic aldehydes. The structure of these compounds was established by IR, 1 H NMR and Mass spectrosopy. The synthesized mannich bases of thiazolidine-2,4-diones were subjected to molecular docking studies with dihydropteroate synthase (DPHS, PDB ID: 3TYE) by using XP GLIDE module of Schrodinger suite and in silico studies by molinspiration online tool. These new compounds (3a-3i) were evaluated for their antimicrobial activity. The compounds 3g and 3h showed good activity against bacteria Salmonella paratyphi, Escherichia coli and fungi Aspergillus niger, Colletotrichum coffeanum comparable to that of standard drugs streptomycin and griseofulvin. Molecular docking studies showed the compound 3h showed good docking score of-5.419 with target protein dihydropteroate synthase.