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.
Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India.
Hrishikesh M
HM
Revankar
Manohar V
MV
Kulkarni
Shrinivas D
SD
Joshi
Uttam A
UA
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects*; D002176:Candida albicans / Q000187:drug effects*; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013293:Enterococcus faecalis / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D009675:Novobiocin / Q000494:pharmacology; D014640:Vancomycin / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003374:Coumarins; D009675:Novobiocin; D014640:Vancomycin
Antimicrobial activity; DNA gyrase subunit A; Ethyl gallate; N-Benzoyl tyrosine ethyl ester; Surflex-Dock