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N6-substituted adenosines. Cytokinin and antitumor activities
Svetlana V. Kolyachkina, Vitali I. Tararov, Cyril S. Alexeev, Dmitry M. Krivosheev, Georgy A. Romanov, Evgenia V. Stepanova, Eliso S. Solomko, Andrey N. Inshakov and Sergey N. Mikhailov
Language English Country Czech Republic Media elektronický zdroj
NLK
ProQuest Central
from 2005-01-01 to 2011
- MeSH
- Adenosine analogs & derivatives MeSH
- Alkylation MeSH
- Cytokinins MeSH
- Nucleosides MeSH
- Antineoplastic Agents MeSH
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.
Institute of Plant Physiology Russian Academy of Sciences Botanicheskaya 35 127276 Moscow Russia
N N Blokhin Cancer Research Center Kashirskoy shosse 24 115478 Moscow Russia
N6-substituted adenosines. Cytokinin and antitumor activities [elektronický zdroj] /
Literatura
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- $a 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.
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