Synthesis and anti-trypanosomal activity of 3′-fluororibonucleosides derived from 7-deazapurine nucleosides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60077344%3A_____%2F21%3A00541603" target="_blank" >RIV/60077344:_____/21:00541603 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/21:00541603 RIV/00216208:11310/21:10430035

Výsledek na webu

<a href="https://doi.org/10.1016/j.bmcl.2021.127957" target="_blank" >https://doi.org/10.1016/j.bmcl.2021.127957</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bmcl.2021.127957" target="_blank" >10.1016/j.bmcl.2021.127957</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and anti-trypanosomal activity of 3′-fluororibonucleosides derived from 7-deazapurine nucleosides

Popis výsledku v původním jazyce

Trypanosoma brucei parasites cause Human African Trypanosomiasis and the current drugs for its treatment are often inefficient and toxic. This urges the need to development of new antitrypanosomal agents. We report the synthesis and biological profiling of 3′-deoxy-3′-fluororibonucleosides derived from 7-deazaadenine nucleosides bearing diverse substituents at position 7. They were synthesized through glycosylation of 6-chloro-7-bromo- or -7-iodo-7-deazapurine with protected 3′-fluororibose followed by cross-coupling reactions at position 7 and/or deprotection. Most of the title nucleosides displayed micromolar or submicromolar activity against Trypanosoma brucei brucei. The most active were the 7-bromo- and 7-iododerivatives which exerted double-digit nanomolar activity against T. b. brucei and T. b. gambiense and no cytotoxicity and thus represent promising candidates for further development.

Název v anglickém jazyce

Synthesis and anti-trypanosomal activity of 3′-fluororibonucleosides derived from 7-deazapurine nucleosides

Popis výsledku anglicky

Trypanosoma brucei parasites cause Human African Trypanosomiasis and the current drugs for its treatment are often inefficient and toxic. This urges the need to development of new antitrypanosomal agents. We report the synthesis and biological profiling of 3′-deoxy-3′-fluororibonucleosides derived from 7-deazaadenine nucleosides bearing diverse substituents at position 7. They were synthesized through glycosylation of 6-chloro-7-bromo- or -7-iodo-7-deazapurine with protected 3′-fluororibose followed by cross-coupling reactions at position 7 and/or deprotection. Most of the title nucleosides displayed micromolar or submicromolar activity against Trypanosoma brucei brucei. The most active were the 7-bromo- and 7-iododerivatives which exerted double-digit nanomolar activity against T. b. brucei and T. b. gambiense and no cytotoxicity and thus represent promising candidates for further development.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

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

Název periodika

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

e-ISSN

1464-3405

Svazek periodika

40

Číslo periodika v rámci svazku

May 15

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

4

Strana od-do

127957

Kód UT WoS článku

000663617900004

EID výsledku v databázi Scopus

2-s2.0-85103100878