Shchegravina, Ekaterina S., Maleev, Alexander A., Ignatov, Stanislav K., Gracheva, Iuliia A., Stein, Andreas, Schmalz, Hans-Guenther, 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:
CreatorsEmailORCIDORCID Put Code
Shchegravina, Ekaterina S.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Maleev, Alexander A.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Ignatov, Stanislav K.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Gracheva, Iuliia A.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Stein, AndreasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Gavryushin, Andrey E.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Zubareva, Anastasiya A.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Svirshchevskaya, Elena V.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Fedorov, Alexey Yu.UNSPECIFIEDorcid.org/0000-0003-4889-8617UNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
COLCHICINE; DERIVATIVES; CYCLIZATIONMultiple languages
Chemistry, MedicinalMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/21009

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