Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00361463" target="_blank" >RIV/61388963:_____/11:00361463 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1135/cccc2011082" target="_blank" >http://dx.doi.org/10.1135/cccc2011082</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1135/cccc2011082" target="_blank" >10.1135/cccc2011082</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides

Popis výsledku v původním jazyce

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium. Key intermediate 6-chloro-7-deazapurine 2'-C-methyl-beta-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl protected 1,2-anhydro-2-C-methylribofuranose. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3',5'-protected 6-chloro-7-deazapurineribofuranoside via 2-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.

Název v anglickém jazyce

Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides

Popis výsledku anglicky

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleosides: 2'-C-methylribonucleosides, arabinonucleosides and 2'-deoxy-2'-fluoroarabinonucleosides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium. Key intermediate 6-chloro-7-deazapurine 2'-C-methyl-beta-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl protected 1,2-anhydro-2-C-methylribofuranose. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3',5'-protected 6-chloro-7-deazapurineribofuranoside via 2-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2011

Kód důvěrnosti údajů

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

Název periodika

Collection of Czechoslovak Chemical Communications

ISSN

0010-0765

e-ISSN

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Svazek periodika

76

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

CZ - Česká republika

Počet stran výsledku

31

Strana od-do

957-988

Kód UT WoS článku

000298002900003

EID výsledku v databázi Scopus

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