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 a Shyamapada BANERJEE

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: 4.000

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/23:00132638

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

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

Štítky

14314010, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 22. 12. 2023 09:16, Mgr. Marie Novosadová 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://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 = {https://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://doi.org/10.1016/j.molstruc.2023.136099.

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