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Synthesis and Evaluation of Quindoline and Its Analogue as Potential Anticancer Agents

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Chemistry of Natural Compounds Aims and scope

Several derivatives of quindoline, 10H-(indolo[3,2-b]quinoline), alkaloids were prepared by the modification of the Pfitzinger quinoline reaction. The conversion of quindoline was 71% while that of another compound, 2,10-bis(dimethylaminoethyl)-indolo[3,2-b]quinoline, was 64%. In the evaluation of the cytotoxicities of the two compounds using five human ovarian cancer cell lines, namely SKOV-3, A2780, A2780R, CHI, and CHIR, quindoline gave minimum inhibitory concentration (IC50) results of 66, 21.5, 24.5, 15.5, and 30 M, respectively whiles the more potent compound, 2,10-bis(dimethylaminoethyl)-indolo[3,2-b]quinoline, gave 6.3, 12.5, 10.5, 8.4, and 12.5 M, respectively. A third compound, 2-(3′-hydroxypropan-1′-yl)-10H-indolo[3,2-b]quinoline, was prepared by the Heck reaction in a yield of 70%.

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Acknowledgment

We thank Prof. S. Neidle of the Cancer Research Campaign Biomolecular Structure Unit, the Institute of Cancer Research, University of London for the biological evaluation and Dr. G. B. Drew and Mr. A. Archie, both of the University of Reading, for the X-ray studies, which will be reported in detail elsewhere.

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Authors and Affiliations

  1. Department of Chemistry, University of Cape Coast, Cape Coast, Ghana

    Yaw Opoku Boahen

  2. Chemistry Department, University of Reading, Reading, RG6 7AD, England

    Yaw Opoku Boahen & John Mann

  3. School of Chemistry, Queen’s University of Belfast, Belfast, BT 9 5AG, N. Ireland

    John Mann

Authors
  1. Yaw Opoku Boahen
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  2. John Mann
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Correspondence to Yaw Opoku Boahen.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2014, pp. 427–429.

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Boahen, Y.O., Mann, J. Synthesis and Evaluation of Quindoline and Its Analogue as Potential Anticancer Agents. Chem Nat Compd 50, 494–497 (2014). https://doi.org/10.1007/s10600-014-0995-8

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  • DOI: https://doi.org/10.1007/s10600-014-0995-8

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