Universität zu Köln

Shchegravina, Ekaterina S., Maleev, Alexander A., Ignatov, Stanislav K., Gracheva, Iuliia A., Stein, Andreas, Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827, Gavryushin, Andrey E., Zubareva, Anastasiya A., Svirshchevskaya, Elena V. and Fedorov, Alexey Yu. ORCID: 0000-0003-4889-8617 (2017). Synthesis and biological evaluation of novel non-racemic indole-containing allocolchicinoids. Eur. J. Med. Chem., 141. S. 51 - 61. ISSY-LES-MOULINEAUX: ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER. ISSN 1768-3254

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Abstract

Two novel indole-containing allocolchicinoids were prepared from naturally occurring coichicine exploiting the Curtius rearrangement and tandem Sonogashira coupling/Pd-catalyzed cyclization as the key transformations. Their cytotoxic properties, apoptosis-inducing activity, tubulin assembly inhibition and short-time cytotoxic effects were investigated. Compound 7 demonstrated the most pronounced anti-cancer activity: IC50 < 1 nM, cell cycle arrest in the G2/M phase, 25% apoptosis induction, as well as lower destructive short-time effects on HT-29 cell line in comparison with colchicine. Docking studies for prepared indole-derived allocolchicine analogues were carried out. (C) 2017 Elsevier Masson SAS. All rights reserved.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Shchegravina, Ekaterina S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Maleev, Alexander A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Ignatov, Stanislav K. UNSPECIFIED UNSPECIFIED UNSPECIFIED Gracheva, Iuliia A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Stein, Andreas UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Gavryushin, Andrey E. UNSPECIFIED UNSPECIFIED UNSPECIFIED Zubareva, Anastasiya A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Svirshchevskaya, Elena V. UNSPECIFIED UNSPECIFIED UNSPECIFIED Fedorov, Alexey Yu. UNSPECIFIED orcid.org/0000-0003-4889-8617 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-210097
DOI:	10.1016/j.ejmech.2017.09.055
Journal or Publication Title:	Eur. J. Med. Chem.
Volume:	141
Page Range:	S. 51 - 61
Date:	2017
Publisher:	ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Place of Publication:	ISSY-LES-MOULINEAUX
ISSN:	1768-3254
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language COLCHICINE; DERIVATIVES; CYCLIZATION Multiple languages Chemistry, Medicinal Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/21009