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Synthesis, Antifungal Evaluation and Molecular Docking Studies of Some Tetrazole Derivatives

Mohammad Hosein Afsarian, Mojtaba Farjam, Elham Zarenezhad, Somayeh Behrouz, Mohammad Navid Soltani Rad

Abstract


A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.


Keywords


‘Click’ cycloaddition, Tetrazoles, Heterogeneous catalyst, Antifungal, Docking.

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DOI: http://dx.doi.org/10.17344/acsi.2019.4992

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Copyright (c) 2019 Mohammad Hosein Afsarian, Mojtaba Farjam, Elham Zarenezhad, Somayeh Behrouz, Mohammad Navid Soltani Rad

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