Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00027162%3A_____%2F23%3AN0000104" target="_blank" >RIV/00027162:_____/23:N0000104 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60077344:_____/23:00574490 RIV/00216224:14310/23:00132638 RIV/62156489:43210/23:43923647

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0022286023011924?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022286023011924?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2023.136099" target="_blank" >10.1016/j.molstruc.2023.136099</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity

Popis výsledku v původním jazyce

Five membered oxa- and thiadiazole derivatives have shown significant biological activity due to their unique bioisosteric properties. Herein, we describe an efficient synthetic approach leading to several novel C-nucleosides containing an oxadiazole or thiadiazole ring system. This work provides for the first-time ability to assemble β-C-nucleosides in a facile manner offering an ideal framework for the possible development of new antiviral and antitumor drugs. All new C-nucleosides were tested for their activity against TBEV and SARS-CoV-2. Two of the synthesized compounds exerted mild anti-SARS-CoV-2 activity, as evidenced by the decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship established with these C-nucleosides.

Název v anglickém jazyce

Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity

Popis výsledku anglicky

Five membered oxa- and thiadiazole derivatives have shown significant biological activity due to their unique bioisosteric properties. Herein, we describe an efficient synthetic approach leading to several novel C-nucleosides containing an oxadiazole or thiadiazole ring system. This work provides for the first-time ability to assemble β-C-nucleosides in a facile manner offering an ideal framework for the possible development of new antiviral and antitumor drugs. All new C-nucleosides were tested for their activity against TBEV and SARS-CoV-2. Two of the synthesized compounds exerted mild anti-SARS-CoV-2 activity, as evidenced by the decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship established with these C-nucleosides.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10607 - Virology

Projekt

<a href="/cs/project/LTAUSA18016" target="_blank" >LTAUSA18016: Výzkum nových nukleosidových analogů jako antivirotik proti medicínsky významným flavivirům</a><br>

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

1872-8014

Svazek periodika

1292

Číslo periodika v rámci svazku

November 2023

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

19

Strana od-do

"136099"

Kód UT WoS článku

001032754800001

EID výsledku v databázi Scopus

2-s2.0-85165686562