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

J 2023

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

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER et. al.

Základní údaje

Originální název

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

Autoři

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK (203 Česká republika, domácí) a Shyamapada BANERJEE (garant)

Vydání

Journal of Molecular Structure, Amsterdam, Elsevier, 2023, 0022-2860

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10606 Microbiology

Stát vydavatele

Nizozemské království

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.800 v roce 2022

Kód RIV

RIV/00216224:14310/23:00132638

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1016/j.molstruc.2023.136099

UT WoS

001032754800001

Klíčová slova anglicky

C -nucleoside; Oxadiazoles; Thiadiazoles; Antiviral; Antitumor; Heterocycles

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 22. 12. 2023 09:16, Mgr. Marie Šípková, DiS.

Anotace

V originále

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 & beta;-Cnucleosides 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.

Citovat

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK a Shyamapada BANERJEE. Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity. Journal of Molecular Structure. Amsterdam: Elsevier, 2023, roč. 1292, November 2023, s. 1-19. ISSN 0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2023.136099.

@article{2352604,
   author = {Penjarla, Srishylam and Reddy, Paidi Yella and Penta, Santhosh and Sanghvi, Yogesh S. and Eyer, Ludek and Stefanik, Michal and Růžek, Daniel and Banerjee, Shyamapada},
   article_location = {Amsterdam},
   article_number = {November 2023},
   doi = {http://dx.doi.org/10.1016/j.molstruc.2023.136099},
   keywords = {C -nucleoside; Oxadiazoles; Thiadiazoles; Antiviral; Antitumor; Heterocycles},
   language = {eng},
   issn = {0022-2860},
   journal = {Journal of Molecular Structure},
   title = {Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity},
   url = {https://doi.org/10.1016/j.molstruc.2023.136099},
   volume = {1292},
   year = {2023}
}

TY  - JOUR
ID  - 2352604
AU  - Penjarla, Srishylam - Reddy, Paidi Yella - Penta, Santhosh - Sanghvi, Yogesh S. - Eyer, Ludek - Stefanik, Michal - Růžek, Daniel - Banerjee, Shyamapada
PY  - 2023
TI  - Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity
JF  - Journal of Molecular Structure
VL  - 1292
IS  - November 2023
SP  - 1-19
EP  - 1-19
PB  - Elsevier
SN  - 00222860
KW  - C -nucleoside
KW  - Oxadiazoles
KW  - Thiadiazoles
KW  - Antiviral
KW  - Antitumor
KW  - Heterocycles
UR  - https://doi.org/10.1016/j.molstruc.2023.136099
N2  - 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 & beta;-Cnucleosides 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.
ER  -

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK a Shyamapada BANERJEE. Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity. \textit{Journal of Molecular Structure}. Amsterdam: Elsevier, 2023, roč.~1292, November 2023, s.~1-19. ISSN~0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2023.136099.

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