Efficient one-pot synthesis of bis-(4-hydroxycoumarin-3yl) methane derivatives using DMAP as a catalyst studies their antibacterial activity and molecular docking

Anil Kumar Bahe, Amit Kumar Harit, Jyotsna Raghuvansi, Sonam Dohare, Ratnesh Das

Department of Chemistry, Dr Harisingh Gour Viswavidyalaya (A Central University) Sagar, Madhya Pradesh, India

ABSTRACT

In the present study, we successfully synthesized a series of 4-hydroxycoumarin with a variety of aromatic aldehydes via a one-pot route. The excellent results of this-(4-hydroxycoumarin-3yl) methane derivatives were obtained in the presence of 5.0 mol % DMAP as a catalyst in Ethanol at room temperature using conventional and ultrasonication methodologies. All the synthesized compounds were bioactive. The synthesized bis-coumarin derivatives were evaluated for the antibacterial activity (in-vitro) against the Staphylococcus aureus, and the results were compared with the standard Kanamycin. Molecular docking analysis was revealed that compound 3,3'-((2-chlorophenyl)methylene) bis (4-hydroxy-2H-chromen-2-one (3c) showed good interaction with bacterial cystathionine gamma-lyase MccB of Staphylococcus aureus protein (-6.8 kcal/mol binding free energy). The results confirmed that majority of the as-synthesized compounds revealed splendid antibacterial activity. The compound 3c (Minimum inhibitory concentration, 40 μg/mL) shows comparable activity in standard with Kanamycin at the same concentrations against Staphylococcus aureus.

Keywords:

Antibacterial activity, Bis-(4-hydroxycoumarin-3yl), DMAP Catalyst, Kanamycin, Staphylococcus aureus (MTCC 1144).