Phosphoramidate pronucleotides of cytostatic 6-aryl-7-deazapurine ribonucleosides

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00360990" target="_blank" >RIV/61388963:_____/11:00360990 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.bmc.2010.11.029" target="_blank" >http://dx.doi.org/10.1016/j.bmc.2010.11.029</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmc.2010.11.029" target="_blank" >10.1016/j.bmc.2010.11.029</a>

Result language

angličtina

Original language name

Phosphoramidate pronucleotides of cytostatic 6-aryl-7-deazapurine ribonucleosides

Original language description

A series of O-phenyl methyl-, ethyl- and benzylalanyl phosphoramidate pronucleotides derived from cytostatic 6-aryl-7-deazapurine ribonucleosides were prepared by the cross-coupling reactions of the 2',3'-isopropylidene protected 6-chloro-7-deazapurine ribonucleoside phosphoramidates with (het)arylboronic acids or -stannanes followed by deprotection. Most of the prepared prodrugs exerted in vitro cytostatic effects against both solid tumor and lymphoid cancer cells within low micromolar range of concentrations. These activities were in general weaker or comparable to the activities of the parent nucleosides. Additional testing of selected prodrugs suggests that the lack of activity improvement over parent nucleosides is not due to the lack of permeability or inefficient catabolism of alanyl-ester by intracellular hydrolases. However, active efflux of prodrugs may play a role in their weak cytotoxic activity.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2011

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Bioorganic & Medicinal Chemistry

ISSN

0968-0896

e-ISSN

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Volume of the periodical

19

Issue of the periodical within the volume

1

Country of publishing house

GB - UNITED KINGDOM

Number of pages

14

Pages from-to

229-242

UT code for WoS article

000285724800022

EID of the result in the Scopus database

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