Synthesis of indole-derived allocolchicine congeners through Pd-catalyzed intramolecular C-H arylation reaction

Nikolay S. Sitnikov, Antonina S. Kokisheva, Georgy K. Fukin, Jörg Martin Neudörfl, Hannah Sutorius, Aram Prokop, Valery V. Fokin, Hans Günther Schmalz, Alexey Yu Fedorov

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18 Citations (Scopus)

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. The synthesis of indole-derived structural analogs of natural antimitotic agent allocolchicine is reported. In a key step, an intramolecular Pd-catalyzed C-H arylation reaction serves to construct the polycyclic ring system, by connecting the two electron-rich arene fragments.

Original languageEnglish
Pages (from-to)6481-6492
Number of pages12
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number29
DOIs
Publication statusPublished - 1 Oct 2014
Externally publishedYes

Keywords

  • Antitumor agents
  • C-H activation
  • Colchicinoids
  • Conformation analysis
  • Heterogeneous catalysis
  • Medicinal chemistry
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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    Sitnikov, N. S., Kokisheva, A. S., Fukin, G. K., Neudörfl, J. M., Sutorius, H., Prokop, A., Fokin, V. V., Schmalz, H. G., & Fedorov, A. Y. (2014). Synthesis of indole-derived allocolchicine congeners through Pd-catalyzed intramolecular C-H arylation reaction. European Journal of Organic Chemistry, 2014(29), 6481-6492. https://doi.org/10.1002/ejoc.201402850