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Synthesis, DNA binding and cytotoxic evaluation of aminoquinoline scaffolds

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Abstract

An effortless synthetic route has been developed for the synthesis of a new class of aminoquinoline substituted isoindolin-1,3-diones from regio-isomerical hydrazinylquinolines with phthalic anhydride in presence of Eaton’s reagent. DNA binding studies of selected isomeric compounds showed interaction with DNA via intercalation mode with higher binding affinity of 4-substituted quinolines rather than 2-substituted counterparts. Further, all compounds were screened for cytotoxic activity against three human cancer cell lines, among them compound 2c outranged standard doxorubicin against CCRF-CEM cell line.

A convenient route to synthesize aminoquinoline substituted isoindolin-1,3-diones using Eaton's reagent as a catalyst has been explored. The DNA binding and in vitro cytotoxicity studies revealed the importance of aminoquinoline scaffolds in cancer treatment.

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Acknowledgements

Our sincere thanks go to SAIF, IIT Madras, Chennai for providing access to their NMR facilities. Dr. K. J. R. P. is grateful to UGC-BSR for the one time research grant.

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Authors and Affiliations

  1. Department of Chemistry, Bharathiar University, Coimbatore, 641046, India

    GOPAL SENTHIL KUMAR & KARNAM JAYARAMPILLAI RAJENDRA PRASAD

  2. Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden, 11800, Penang, Malaysia

    MOHAMED ASHRAF ALI & TAN SOO CHOON

  3. New Drug Discovery Research, Department of Medicinal Chemistry, Alwar Pharmacy College, Alwar, Rajasthan, 301030, India

    MOHAMED ASHRAF ALI

  4. New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan, 301030, India

    MOHAMED ASHRAF ALI

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  1. GOPAL SENTHIL KUMAR
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Correspondence to KARNAM JAYARAMPILLAI RAJENDRA PRASAD.

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Supporting Information (SI)

Copies of 1H and 13C NMR spectra for all newly synthesized compounds are available at www.ias.ac.in/chemsci.

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KUMAR, G.S., ALI, M.A., CHOON, T.S. et al. Synthesis, DNA binding and cytotoxic evaluation of aminoquinoline scaffolds. J Chem Sci 128, 391–400 (2016). https://doi.org/10.1007/s12039-015-1025-5

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  • DOI: https://doi.org/10.1007/s12039-015-1025-5

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