Shchegravina, Ekaterina S., Knyazev, Dmitry I., Beletskaya, Irina P., Svirshchevskaya, Elena V., Schmalz, Hans-Guenther 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:
CreatorsEmailORCIDORCID Put Code
Shchegravina, Ekaterina S.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Knyazev, Dmitry I.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Beletskaya, Irina P.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Svirshchevskaya, Elena V.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Fedorov, Alexey Yu.UNSPECIFIEDorcid.org/0000-0003-4889-8617UNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
BIOLOGICAL EVALUATION; COLCHICINE; TUBULIN; DESIGN; TRIAL; ANTICANCER; ANALOGS; AGENTS; SITEMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/25386

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