4.0 Article

1,3-Dipolar Cycloaddition Reactions for the Synthesis of Novel Oxindole Derivatives and Their Cytotoxic Properties

Journal

ACS COMBINATORIAL SCIENCE
Volume 19, Issue 10, Pages 633-639

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.7b00044

Keywords

1,3-dipolar cycloaddition; amino acid; but-2-ynedioates; N-substituted oxindole derivatives; microwave assisted; aqueous medium; cytotoxic properties

Funding

  1. UGC, New Delhi
  2. Council of Scientific & Industrial Research (CSIR), New Delhi under the XIIth Five Year Plan Project Affordable Cancer Therapeutics (ORIGIN) [CSC0108]

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The multicomponent reaction between isatin, amino acid, but-2-ynedioates, and phenacyl bromide has been developed using microwave irradiation under catalyst and base-free conditions in aqueous medium. This synthetic protocol is useful for the synthesis of various functionalized spirooxindole derivatives. This MCR exhibits a broad substrate scope with excellent yields and shorter reaction time. Additionally the synthesized spirooxindole derivatives were evaluated for their anticancer activity against three human cancer cell lines: MCF-7 (breast), A549 (lung), and HeLa cervical. Most of the compounds showed moderate to potent cytotoxic activity against the tested cell lines.

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