Universität zu Köln

Shchegravina, Ekaterina S., Knyazev, Dmitry I., Beletskaya, Irina P., Svirshchevskaya, Elena V., Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Fedorov, Alexey Yu. ORCID: 0000-0003-4889-8617 (2016). Synthesis of Nonracemic Pyrrolo-allocolchicinoids Exhibiting Potent Cytotoxic Activity. Eur. J. Org. Chem., 2016 (34). S. 5620 - 5624. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

An efficient eight-step semisynthetic approach towards nonracemic pyrrolo-allocolchicinoids starting from natural colchicine was developed by exploiting Pd-catalyzed domino Sonogashira coupling/5-endo-dig cyclization of a 2-iodo-trifluoroacetanilide intermediate to build up the heterocyclic ring system. The N-Me substitution of the pyrrole ring enhanced the antitumor activity of the prepared molecules by 2-3 orders of magnitude. Among the active compounds, the N-methylated colchicinoid exhibited powerful cytotoxic and antiproliferative properties at concentrations < 1 nM.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Shchegravina, Ekaterina S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Knyazev, Dmitry I. UNSPECIFIED UNSPECIFIED UNSPECIFIED Beletskaya, Irina P. UNSPECIFIED UNSPECIFIED UNSPECIFIED Svirshchevskaya, Elena V. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Fedorov, Alexey Yu. UNSPECIFIED orcid.org/0000-0003-4889-8617 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-253869
DOI:	10.1002/ejoc.201601069
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2016
Number:	34
Page Range:	S. 5620 - 5624
Date:	2016
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
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 BIOLOGICAL EVALUATION; COLCHICINE; TUBULIN; DESIGN; TRIAL; ANTICANCER; ANALOGS; AGENTS; SITE Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/25386