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New N ‐phenylacetamide‐linked 1,2,3‐triazole‐tethered coumarin conjugates: Synthesis, bioevaluation, and molecular docking study
Author(s) -
Akolkar Satish V.,
Nagargoje Amol A.,
Shaikh Mubarak H.,
Warshagha Murad Z. A.,
Sangshetti Jaiprakash N.,
Damale Manoj G.,
Shingate Bapurao B.
Publication year - 2020
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000164
Subject(s) - chemistry , coumarin , docking (animal) , triazole , 1,2,3 triazole , click chemistry , candida albicans , stereochemistry , adme , cryptococcus neoformans , antifungal drug , miconazole , biochemistry , combinatorial chemistry , in vitro , organic chemistry , microbiology and biotechnology , biology , antifungal , medicine , nursing
Abstract A series of new 1,2,3‐triazole‐tethered coumarin conjugates linked by N ‐phenylacetamide was efficiently synthesized via the click chemistry approach in excellent yields. The synthesized conjugates were evaluated for their in vitro antifungal and antioxidant activities. Antifungal activity determination was carried out against fungal strains such as Candida albicans , Fusarium oxysporum , Aspergillus flavus , Aspergillus niger and Cryptococcus neoformans . Compounds 7b , 7d , 7e , 8b and 8e displayed higher potency than the standard drug miconazole, with lower minimum inhibitory concentration values. Also, compound 7a exhibited potential radical scavenging activity as compared with the standard antioxidant butylated hydroxytoluene. In addition, a molecular docking study of the newly synthesized compounds was carried out, and the results showed a good binding mode at the active site of the fungal ( C. albicans ) P450 cytochrome lanosterol 14α‐demethylase enzyme. Furthermore, the synthesized compounds were also tested for ADME properties, and they demonstrated potential as good candidates for oral drugs.