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Synthesis and Molecular Modelling Studies of Coumarin and 1‐Aza‐Coumarin Linked Miconazole Analogues and Their Antimicrobial Properties
Author(s) -
Sutar Suraj M.,
Savanur Hemantkumar M.,
Malunavar Shruti S.,
Pawashe Geeta M.,
Aridoss Gopalakrishnan,
Kim Kang Min,
Lee Jin Young,
Kalkhambkar Rajesh G.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903572
Subject(s) - coumarin , benzimidazole , miconazole , chemistry , stereochemistry , antimicrobial , imidazole , alkyl , combinatorial chemistry , organic chemistry , biology , microbiology and biotechnology , antifungal
A series of coumarin and 1‐Aza coumarin analogues of miconazole (5 a‐6 e) were synthesized from 2‐bromo‐1‐(2,4‐dichlorophenyl)ethanone and diversification was achieved by synthesizing coumarin‐benzimidazole (7 a‐7 e) and 1‐aza coumarin‐benzimidazole (8 a‐8 e) hybrids of miconazole and evaluated for in‐vitro anti‐microbial activities. Among the tested compounds, 8 b‐8 e were found to be effective as anti‐fungal against C. albicans, C. utilis and C. krusei , with activity compared to that of the standard. Comparative docking studies with mevalonate‐5‐diphosphatedecarboxylase shows better binding affinity than imidazole counterparts which is primarily attributed to extended π‐alkyl interactions facilitated by benzimidazole.