Universität zu Köln

Voitovich, Yuliya V., Shegravina, Ekaterina S., Sitnikov, Nikolay S., Faerman, Vladimir I., Fokin, Valery V., Schmalz, Hans-Gunther ORCID: 0000-0003-0489-1827, Combes, Sebastien, Allegro, Diane, Barbier, Pascal, Beletskaya, Irina P., Svirshchevskaya, Elena V. and Fedorov, Alexey Yu. ORCID: 0000-0003-4889-8617 (2015). Synthesis and Biological Evaluation of Furanoallocolchicinoids. J. Med. Chem., 58 (2). S. 692 - 705. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-4804

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Abstract

A series of conformationally flexible furan-derived allocolchicinoids was prepared from commercially available colchicine in good to excellent yields using a three-step reaction sequence. Cytotoxicity studies indicated the potent activity of two compounds against human epithelial and lymphoid cell lines (AsPC-1, HEK293, and Jurkat) as well as against Wnt-1 related murine epithelial cell line W1308. The results of in vitro experiments demonstrated that the major effect of these compounds was the induction of cell cycle arrest in the G2/M phase as a direct consequence of effective tubulin binding. In vivo testing of the most potent furanoallocolchicinoid <bold>10c</bold> using C57BL/6 mice inoculated with Wnt-1 tumor cells indicated significant inhibition of the tumor growth.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Voitovich, Yuliya V. UNSPECIFIED UNSPECIFIED UNSPECIFIED Shegravina, Ekaterina S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Sitnikov, Nikolay S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Faerman, Vladimir I. UNSPECIFIED UNSPECIFIED UNSPECIFIED Fokin, Valery V. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Gunther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Combes, Sebastien UNSPECIFIED UNSPECIFIED UNSPECIFIED Allegro, Diane UNSPECIFIED UNSPECIFIED UNSPECIFIED Barbier, Pascal UNSPECIFIED UNSPECIFIED UNSPECIFIED Beletskaya, Irina P. 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:38-414445
DOI:	10.1021/jm501678w
Journal or Publication Title:	J. Med. Chem.
Volume:	58
Number:	2
Page Range:	S. 692 - 705
Date:	2015
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-4804
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 INTRAMOLECULAR NICHOLAS REACTIONS; COMBRETASTATIN A4 PHOSPHATE; PHASE-I TRIAL; 4-ARYLCOUMARIN ANALOGS; COLCHICINE SITE; ANTINEOPLASTIC AGENTS; COMMON PHARMACOPHORE; ANTITUMOR-ACTIVITY; ANTICANCER AGENTS; A-4 ANALOGS Multiple languages Chemistry, Medicinal Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/41444