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Green synthesis, biochemical and quantum chemical studies of steroidal oximes

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Abstract

Microwave-assisted condensation of steroidal ketones with hydroxylamine under solvent-free condition in presence of basic alumina as solid support yielded the title compounds. The compounds were subjected for their in vitro antimicrobial against a set of pathogenic bacteria and fungi. The 3β-chloro-5α-cholestan-6-one oxime (6) showed highest antimicrobial activity. Steroidal oximes were also screened for their in vitro anthelmintic activity against earthworms. Chloro compound was found to be a more potent anthelmintic agent when compared with albendazole. The in silico docking technique has been applied to ascertain the potential binding sites of the compounds with the pathogenic receptor. The binding modes of a representative compound 6 were accessed on the basis of molecular docking studies. Moreover the structure-antimicrobial activity relationships were studied using some physicochemical and quantum-chemical parameters with GAMESS interface as well as WebMO Job Manager by DFT at B3LYP/6-31G & STO-3G level of theory.

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  1. Division of Bioscience, Dongguk University, Gyeongju, 780-714, Korea

    Mahboob Alam & Dong-Ung Lee

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Alam, M., Lee, DU. Green synthesis, biochemical and quantum chemical studies of steroidal oximes. Korean J. Chem. Eng. 32, 1142–1150 (2015). https://doi.org/10.1007/s11814-014-0314-x

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