Synthesis, biological evaluation and docking studies of 4-aryloxymethyl coumarins derived from substructures and degradation products of vancomycin

Two series of 4-aryloxymethyl coumarins derived from the reaction of 4-bromomethyl coumarins with ethyl gallate and ethyl ester of N-Benzoyl tyrosine have been synthesized. Gallate ethers 3a–3g and tyrosine derivatives 4e–4j were most effective against Entercoccus faecalis. They were also found to be effective against Aspergillus niger and Candida albicans. Comparative docking studies with novobiocin have indicated better binding ability and higher ‘C’ score values than novobiocin. [Display omitted] 4-Aryloxymethyl coumarins possessing gallate and tyrosinate moieties have been found to be specifically active against Enteroccocus faecalis, which is also supported by docking studies using bacterial DNA gyrase. •Coumarin ethers from residues of vancomycin are most effective against Enteroccocus faecalis.•Coumarin ether of N-benzoyl tyrosinate show greater inhibition of fungal strains.•Docking studies showed better docking with DNA gyrase than novobiocin.