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Letters in Drug Design & Discovery

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ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

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Research Article

An Ultrasound-assisted Three Component Protocol for the Regio and Stereo-selective Synthesis of Some Novel Dispiroheterocycles and Their Biological Evaluation as Anti-inflammatory, Anti-obesity Agents

Author(s): Sanjeev Kumar, Bhavna Saroha, Ekta Lathwal, Gourav Kumar, Suresh Kumar*, Ramesh Kumar, Priyanka Arya and Neera Raghav

Volume 21, Issue 1, 2024

Published on: 10 April, 2023

Page: [133 - 142] Pages: 10

DOI: 10.2174/1570180820666230306115855

Price: $65

Abstract

Background: The increasing utilization of spiro compounds in drug discovery, led us to design and synthesize regioselectively some novel dispiroheterocycles, by a standard 1,3-dipolar cycloaddition reaction between 6-hydroxyaurone and in situ generated azomethine ylides, using ultra-sonication as green energy source. These results are first of its kind in the literature reported so far for the similar conditions. After confirmation of the proposed structures spectroscopically, using 1H NMR, 13C NMR and FT-IR spectral data, all the compounds are screened for their potential biological activities.

Methods: Three component protocol, that contain (Z)-2-benzylidene-6-hydroxybenzofuran-3(2H)-one, sarcosine and unsubstituted isatin. In which azomethine ylides react with olefinic dipolarophiles through 1,3-dipolar cycloaddition, which is highly regio- and stero-selective way in situ. Structures of the proposed products have been confirmed using 1H NMR, 13C NMR and FT-IR spectral data.

Results: In order to screen the potential biological activities of the synthesized compounds, their effect was observed on trypsin, amylase and lipase activities. Differential effect has been observed. Trypsin was substantially activated whereas an inhibitory effect was observed for amylase and lipase supported by in silico studies.

Conclusion: Synthesis of six novel 6-hydroxy-1'-methyl-4'-phenyl-3H-dispiro[benzofuran-2,3'- pyrrolidine-2',3''-indoline]-2'',3-dione derivatives have been made using a multicomponent greener protocol. These synthesized compounds have exhibited differential effects toward trypsin, amylase and lipase well supported by in silico studies. Thus, the present study highlights their potential use as antiinflammatory and anti-obesity agents.

Keywords: Aurones, spiro compounds, three-component reaction, dipolar cycloaddition reaction, azomethine ylides, spirooxindole, trypsin, amylase, lipase.

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