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

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Abstract

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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Acknowledgments

The Authors thank the Council of Scientific and Industrial Research CSIR-SRF (Ref No. 09/472(0145)/2K10-EMR-I) New Delhi, India, for financial assistance. We acknowledge Dr. Aathirajan, Professor, Cell culture Laboratory, KMCH College of Pharmacy, Coimbatore for evaluating cytotoxicity of synthesized compounds for Cervical cancer cell lines. Dr. Karvembu, Head of the Department of Chemistry, National Institute of Technology, Trichy is gratefully acknowledged for providing optical rotatory dispersion studies. The authors thank SAIF, NMR Research Centre, Bangalore SAIF, IIT Chennai for spectral study.

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Authors and Affiliations

  1. School of Chemical Sciences, Bharathiar University, Coimbatore, 641046, Tamilnadu, India

    Mathan Sankaran, Chokkalingam Uvarani, Kumarasamy Chandraprakash & Palathurai Subramaniam Mohan

  2. Rajiv Gandhi Centre for Biotechnology, Thycaud, Trivandrum, 695 014, India

    Swathi U. Lekshmi & Sengupta Suparna

  3. Theoretical & Computational Chemistry, School of Chemistry, Cardiff University, Cardiff, CF10 3AT, UK

    James Platts

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  1. Mathan Sankaran
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Correspondence to Palathurai Subramaniam Mohan.

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Sankaran, M., Uvarani, C., Chandraprakash, K. et al. A regioselective multicomponent protocol for the synthesis of novel bioactive 4-hydroxyquinolin-2(1H)-one grafted monospiropyrrolidine and thiapyrrolizidine hybrids. Mol Divers 18, 269–283 (2014). https://doi.org/10.1007/s11030-013-9498-y

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