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.
Highlights
Tetrazole and its derivatives have attracted considerable interest in recent years because of their unique structure and wide range of applications.[1]
Heterocyclic compounds exhibiting tetrazole structures are known as bioactive compounds, encompassing a broad spectrum of biological activities such as antihypertensive,[2] antibacterial,[3,4] antifungal,[5] anticonvulsant,[6] analgesics,[7] anti-inflammatory,[8] antitubercular,[9] anticancer,[10] antineoplastic,[11] antial
The syntheses of tetrazole moieties are very essential in modern medicinal chemistry, since they can behave as bioisosters for carboxylate moieties
Summary
Tetrazole and its derivatives have attracted considerable interest in recent years because of their unique structure and wide range of applications.[1] Heterocyclic compounds exhibiting tetrazole structures are known as bioactive compounds, encompassing a broad spectrum of biological activities such as antihypertensive,[2] antibacterial,[3,4] antifungal,[5] anticonvulsant,[6] analgesics,[7] anti-inflammatory,[8] antitubercular,[9] anticancer,[10] antineoplastic,[11] antial-.
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