Collect. Czech. Chem. Commun.
2011, 76, 1361-1378
https://doi.org/10.1135/cccc2011114
Published online 2011-11-20 19:55:52
N6-substituted adenosines. Cytokinin and antitumor activities
Svetlana V. Kolyachkinaa, Vitali I. Tararova, Cyril S. Alexeeva, Dmitry M. Krivosheevb, Georgy A. Romanovb, Evgenia V. Stepanovac, Eliso S. Solomkoc, Andrey N. Inshakovc and Sergey N. Mikhailova,*
a Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, 119991 Moscow, Russia
b Institute of Plant Physiology, Russian Academy of Sciences, Botanicheskaya 35, 127276 Moscow, Russia
c N.N. Blokhin Cancer Research Center, Kashirskoy shosse 24, 115478 Moscow, Russia
Abstract
A series of N6-adenosine derivatives were synthesized by alkylation of N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (1) with alkyl halides and alcohols. It was shown that propargyl derivative 2a is a good substrate for copper(I) catalyzed Huisgen [3+2] cycloaddition with azides. This click-reaction can be used for preparation of the libraries of 1,2,3-triazolyl modified adenosines. Biological activities of N6-adenosines were studied in two plant and six human cancer cell assays. The remarkable parallel between cytokinin and cytotoxic activities was found. The most cytokinin active compounds 3c–3e at the same time appeared to be the most potent cytotoxic agents.
Keywords: Nucleosides; Adenosine derivatives; Alkylation; Huisgen [3+2] cycloaddition; Cytokinins; Anticancer activity; Click chemistry; Antitumor agents.
References: 40 live references.
