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

Hrishikesh M Revankar; Manohar V Kulkarni; Shrinivas D Joshi; Uttam A More

doi:10.1016/j.ejmech.2013.10.047

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

Eur J Med Chem. 2013:70:750-7. doi: 10.1016/j.ejmech.2013.10.047. Epub 2013 Oct 25.

Authors

Hrishikesh M Revankar¹, Manohar V Kulkarni, Shrinivas D Joshi, Uttam A More

Affiliation

¹ Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India.

PMID: 24239622
DOI: 10.1016/j.ejmech.2013.10.047

Abstract

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.

Keywords: Antimicrobial activity; DNA gyrase subunit A; Ethyl gallate; N-Benzoyl tyrosine ethyl ester; Surflex-Dock.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Aspergillus niger / drug effects*
Candida albicans / drug effects*
Coumarins / chemical synthesis
Coumarins / chemistry
Coumarins / pharmacology*
Enterococcus faecalis / drug effects*
Microbial Sensitivity Tests
Models, Molecular
Molecular Structure
Novobiocin / pharmacology
Vancomycin / chemistry*

Substances

Anti-Bacterial Agents
Antifungal Agents
Coumarins
Novobiocin
Vancomycin