Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7‑Deazapurine Ribonucleosides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73584060" target="_blank" >RIV/61989592:15110/17:73584060 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/17:00475217 RIV/00216208:11310/17:10359782

Výsledek na webu

<a href="http://pubs.acs.org/doi/10.1021/acs.jmedchem.6b01766" target="_blank" >http://pubs.acs.org/doi/10.1021/acs.jmedchem.6b01766</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jmedchem.6b01766" target="_blank" >10.1021/acs.jmedchem.6b01766</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7‑Deazapurine Ribonucleosides

Popis výsledku v původním jazyce

Two isomeric series of new thieno-fused 7-deazapurine ribonucleosides (derived from 4-substituted thieno[2′,3′:4,5]pyrrolo[2,3-d]pyrimidines and thieno-3′,2′:4,5]pyrrolo[2,3-d]pyrimidines) were synthesized by a sequence involving Negishi coupling of 4,6-dichloropyrimidine with iodothiophenes, nucleophilic azidation, and cyclization of tetrazolopyrimidines, followed by glycosylation and cross-couplings or nucleophilic substitutions at position 4. Most nucleosides (from both isomeric series) exerted low micromolar or submicromolar in vitro cytostatic activities against a broad panel of cancer and leukemia cell lines and some antiviral activity against HCV. The most active were the 6-methoxy, 6-methylsulfanyl, and 6-methyl derivatives, which were highly active to cancer cells and less toxic or nontoxic to fibroblasts.

Název v anglickém jazyce

Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7‑Deazapurine Ribonucleosides

Popis výsledku anglicky

Two isomeric series of new thieno-fused 7-deazapurine ribonucleosides (derived from 4-substituted thieno[2′,3′:4,5]pyrrolo[2,3-d]pyrimidines and thieno-3′,2′:4,5]pyrrolo[2,3-d]pyrimidines) were synthesized by a sequence involving Negishi coupling of 4,6-dichloropyrimidine with iodothiophenes, nucleophilic azidation, and cyclization of tetrazolopyrimidines, followed by glycosylation and cross-couplings or nucleophilic substitutions at position 4. Most nucleosides (from both isomeric series) exerted low micromolar or submicromolar in vitro cytostatic activities against a broad panel of cancer and leukemia cell lines and some antiviral activity against HCV. The most active were the 6-methoxy, 6-methylsulfanyl, and 6-methyl derivatives, which were highly active to cancer cells and less toxic or nontoxic to fibroblasts.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

<a href="/cs/project/LO1304" target="_blank" >LO1304: Podpora udržitelnosti Ústavu molekulární a translační medicíny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Journal of Medicinal Chemistry

ISSN

0022-2623

e-ISSN

—

Svazek periodika

60

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

14

Strana od-do

2411-2424

Kód UT WoS článku

000397546000018

EID výsledku v databázi Scopus

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