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

S. Yu. Bukhvalova; A. A. Maleev; Yu. A. Gracheva; Yu. V. Voitovich; S. K. Ignatov; E. V. Svirshchevskaya; A. Yu. Fedorov

doi:10.1007/s11172-019-2689-7

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

Authors: Bukhvalova S.Y.¹^,2, Maleev A.A.², Gracheva Y.A.², Voitovich Y.V.², Ignatov S.K.², Svirshchevskaya E.V.³, Fedorov A.Y.²
Affiliations:
1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences
2. N. I. Lobachevsky State University of Nizhny Novgorod
3. M. M. Shemyakin—Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences
Issue: Vol 68, No 12 (2019)
Pages: 2205-2215
Section: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/243550
DOI: https://doi.org/10.1007/s11172-019-2689-7
ID: 243550

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Abstract
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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.

Keywords

antitumor agents, colchicine, tubulin, benzo [b] oxepines, gold-catalyzed cyclization

About the authors

S. Yu. Bukhvalova

G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences; N. I. Lobachevsky State University of Nizhny Novgorod

Email: afedorovnn@yandex.ru
Russian Federation, 49 ul. Tropinina, Nizhny Novgorod, 603137; 23 prosp. Gagarina, Nizhny Novgorod, 603950