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

Result code in 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>
Alternative codes found
RIV/60077344:_____/23:00574490 RIV/00216224:14310/23:00132638 RIV/62156489:43210/23:43923647
Result on the web
<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>

Result language
angličtina
Original language name
Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity
Original language description
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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10607 - Virology

Project
<a href="/en/project/LTAUSA18016" target="_blank" >LTAUSA18016: Search for novel nucleoside analogs as antivirals against medically important flaviviruses.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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