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Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine

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Abstract

New allocolchicine derivatives bearing 2,3-dihydrobenzo[b]oxepine moiety were synthesized via gold-catalyzed cyclization as a key synthetic step. The obtained 2,3-dihydrobenzo[b]oxepine-containing allocolchicinoids possess cytotoxic activity against HEK293, PANC-1, COL0357, HeLa, and Colon26 cancer cell lines at low micromolar range of concentrations.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603137, Nizhny Novgorod, Russian Federation

    S. Yu. Bukhvalova

  2. N. I. Lobachevsky State University of Nizhny Novgorod, 23 prosp. Gagarina, 603950, Nizhny Novgorod, Russian Federation

    S. Yu. Bukhvalova, A. A. Maleev, Yu. A. Gracheva, Yu. V. Voitovich, S. K. Ignatov & A. Yu. Fedorov

  3. M. M. Shemyakin—Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117997, Moscow, Russian Federation

    E. V. Svirshchevskaya

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  1. S. Yu. Bukhvalova
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  2. A. A. Maleev
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  3. Yu. A. Gracheva
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  4. Yu. V. Voitovich
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  5. S. K. Ignatov
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  6. E. V. Svirshchevskaya
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  7. A. Yu. Fedorov
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Correspondence to A. Yu. Fedorov.

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This work was financially supported by the Russian Science Foundation (Project No. 19-13-00158).

Based on the materials of the 4th Russian Conference on Medicinal Chemistry with International participation (June 9–14, 2019, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2205–2215, December, 2019.

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Bukhvalova, S.Y., Maleev, A.A., Gracheva, Y.A. et al. Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine. Russ Chem Bull 68, 2205–2215 (2019). https://doi.org/10.1007/s11172-019-2689-7

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