Coumarin thiopropionic Acids: Syntheses, Characterization, and Comparison of Docking-DFT Studies on their Antimicrobial Activity

Abstract

Three coumarin thiopropionic acid (4, 7, and 10) derivatives have been synthesized from the key-intermediates 4-(chloromethyl)-6-methyl-2H-chromen-2-one (3), 4-(chloromethyl)-6-hydroxy-2H-chromen-2-one (6), and 4-(chloromethyl)-2H-benzo[g]chromen-2-one (9). These compounds have been characterized by IR, ¹H-NMR, ¹³C-NMR, Mass, and CHN analysis. These are subjected to antimicrobial-, anticancer-, and DNA cleaving studies. The docking patterns for the above derivatives 4, 7, and 10 with 1FIQ protein have been studied. Compound 4 has a lower binding energy (-225.46 Kcal/mol) as compared to that of other derivatives (7 and 10). DFT calculations were performed using Gaussian 09 software. Compound 4 showed the highest antimicrobial activity. DFT and docking studies agreed well with the experimental antimicrobial activity.