Sitnikov, Nikolay S., Kokisheva, Antonina S., Fukin, Georgy K., Neudoerfl, Joerg-Martin, Sutorius, Hannah, Prokop, Aram, Fokin, Valery V., Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Fedorov, Alexey Yu (2014). Synthesis of Indole-Derived Allocolchicine Congeners through Pd-Catalyzed Intramolecular C-H Arylation Reaction. Eur. J. Org. Chem., 2014 (29). S. 6481 - 6493. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

The synthesis of several new heterocyclic structural analogs of the natural antimitotic agent allocolchicine is reported. As a key step an intramolecular Pd-catalyzed C-H arylation reaction was used to close the seven-membered ring fused with two electron-rich aryl fragments. The stereostructure of the target compounds was determined by X-ray crystal analysis. The primary biological assessment of the synthesized compounds was carried out on human lymphoma cells. Several allocolchicinoids were determined to possess antiproliferative and apoptosis-inducing activity in the micromolar concentration range.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Sitnikov, Nikolay S.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kokisheva, Antonina S.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Fukin, Georgy K.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Sutorius, HannahUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Prokop, AramUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Fokin, Valery V.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
Fedorov, Alexey YuUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-427964
DOI: 10.1002/ejoc.201402850
Journal or Publication Title: Eur. J. Org. Chem.
Volume: 2014
Number: 29
Page Range: S. 6481 - 6493
Date: 2014
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:
KeywordsLanguage
FRIEDEL-CRAFTS ACYLATION; ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS; ASYMMETRIC-SYNTHESIS; CONJUGATE REDUCTION; NICHOLAS REACTIONS; NATURAL-PRODUCTS; ONE-POT; COLCHICINE; TUBULIN; BONDMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/42796

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