title: Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones.
abstract: A series of novel 3-(1,2,4-triazol-1-yl)flavanones were synthesized based on the N-phenethylazole pharmacophore of azole antifungals. The results of antifungal assay revealed that 4'-fluoroflavanone derivative 4c exhibited the best profile of activity against Candida and Saccharomyces strains. Compound 4c was 4-16 times more potent than reference drug fluconazole against Candida albicans and Saccharomyces cerevisiae. The molecular docking study with lanosterol 14α-demethylase, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents. The favorable drug-like property of compound 4c makes 3-(1,2,4-triazol-1-yl)flavanone prototype as a promising lead for the future development of azole antifungal agents.
authors.affiliation: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran. sd_emami@yahoo.com
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Shahaboddin
authors.initials: S
authors.lastname: Shojapour
authors.forename: Mohammad Ali
authors.initials: MA
authors.lastname: Faramarzi
authors.forename: Nasrin
authors.initials: N
authors.lastname: Samadi
authors.forename: Hamid
authors.initials: H
authors.lastname: Irannejad
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D020134:Catalytic Domain; D060326:Chemistry Techniques, Synthetic; D044950:Flavanones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects* / Q000201:enzymology; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D058886:Sterol 14-Demethylase / Q000737:chemistry / Q000378:metabolism
chemical_list: D000935:Antifungal Agents; D044950:Flavanones; D058886:Sterol 14-Demethylase
keywords: 1,2,4-Triazole; Antifungal activity; Azole antifungals; Docking study; Drug-likeness; Flavanones