Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F13%3A10159265" target="_blank" >RIV/00216208:11310/13:10159265 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/13:00393973

Výsledek na webu

<a href="http://dx.doi.org/10.1002/cmdc.201300047" target="_blank" >http://dx.doi.org/10.1002/cmdc.201300047</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cmdc.201300047" target="_blank" >10.1002/cmdc.201300047</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

Popis výsledku v původním jazyce

A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2-deoxy-2-fluororibo- and 2-deoxy-2,2-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2-deoxy-2-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3- and 5-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-

Název v anglickém jazyce

Synthesis and Cytostatic and Antiviral Activities of 2 '-Deoxy-2 ',2 '-difluororibo- and 2 '-Deoxy-2 '-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

Popis výsledku anglicky

A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2-deoxy-2-fluororibo- and 2-deoxy-2,2-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2-deoxy-2-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3- and 5-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-

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

<a href="/cs/project/GAP207%2F11%2F0344" target="_blank" >GAP207/11/0344: Kombinatoriální a racionální přístupy pro syntézu a studium nových modifikovaných nukleosidů s cytostatickou a antimikrobiální aktivitou</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

ChemMedChem

ISSN

1860-7179

e-ISSN

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Svazek periodika

8

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

15

Strana od-do

832-846

Kód UT WoS článku

000318245300016

EID výsledku v databázi Scopus

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