4.5 Article

A regioselective multicomponent protocol for the synthesis of novel bioactive 4-hydroxyquinolin-2(1H)-one grafted monospiropyrrolidine and thiapyrrolizidine hybrids

Journal

MOLECULAR DIVERSITY
Volume 18, Issue 2, Pages 269-283

Publisher

SPRINGER
DOI: 10.1007/s11030-013-9498-y

Keywords

Multicomponent reaction; Azomethine ylide; 1,3-Dipolar cycloaddition; Non-covalent interaction; Cytotoxicity; MCRs

Funding

  1. Council of Scientific and Industrial Research CSIR-SRF New Delhi, India [09/472(0145)/2K10-EMR-I]

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An expedient route toward the synthesis of 4-hydroxyquinolone grafted spiropyrrolidines or pyrrolizidines has been accomplished through 1,3-dipolar cycloaddition reaction of various azomethine ylides derived from isatin or acenaphthalene and sarcosine with 4-hydroxyquinolone derivatives as dipolarophile. The regio and stereo chemical outcome of the cycloaddition reaction is ascertained by X-ray crystallographic studies and spectroscopic techniques of the cycloadducts. Furthermore, cytotoxicity evaluation of selected compounds showed significant inhibition of cell proliferation against cervical as well as colon cancer cell lines.

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