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Synthesis of Indole‐Derived Allocolchicine Congeners through Pd‐Catalyzed Intramolecular C‐H Arylation Reaction
Author(s) -
Sitnikov Nikolay S.,
Kokisheva Antonina S.,
Fukin Georgy K.,
Neudörfl JörgMartin,
Sutorius Hannah,
Prokop Aram,
Fokin Valery V.,
Schmalz HansGünther,
Fedorov Alexey Yu.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402850
Subject(s) - chemistry , intramolecular force , indole test , stereochemistry , ring (chemistry) , catalysis , aryl , combinatorial chemistry , intramolecular reaction , organic chemistry , alkyl
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.