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“On water” synthesis of dibenzo-[1,4]-diazepin-1-ones using L-proline as an organocatalyst and under catalyst-free conditions, and their evaluation as α-glucosidase inhibitors

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Abstract

Functionalized dibenzo-[1,4]-diazepin-1-ones were synthesized using the “on-water” concept in the presence of L-proline (organocatalyst; 20 mol%) and under catalyst free conditions (sealed tube) in an aqueous medium. The resulting molecules were tested (in vitro) for α-glucosidase (isolated from Saccharomyces cerevisiae) enzyme inhibition using acarbose as a standard drug (IC50 32.47 ± 1.64). The enzyme inhibition kinetic analysis of selected molecules showed the competitive mode of inhibition (best result; IC50 39.31 ± 1.68) against α-glucosidase. Molecular docking studies of these compounds with the MAL12 homology model showed HIS279A as a major interacting residue in the binding site of the protein which is a similar binding mode consistent with the binding of acarbose.

Graphical abstract: “On water” synthesis of dibenzo-[1,4]-diazepin-1-ones using l-proline as an organocatalyst and under catalyst-free conditions, and their evaluation as α-glucosidase inhibitors

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Publication details

The article was received on 28 Mar 2017, accepted on 18 Jul 2017 and first published on 19 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01021D
Citation: New J. Chem., 2017, Advance Article
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    “On water” synthesis of dibenzo-[1,4]-diazepin-1-ones using L-proline as an organocatalyst and under catalyst-free conditions, and their evaluation as α-glucosidase inhibitors

    S. Nagaraju, O. Perumal P., K. Divakar, B. Paplal and D. Kashinath, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01021D

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