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

0574490 - BC 2024 RIV NL eng J - Článek v odborném periodiku
Penjarla, S. - Reddy, P.Y. - Penta, S. - Sanghvi, Y.S. - Eyer, Luděk - Štefánik, M. - Růžek, Daniel - Banerjee, S.
Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity.
Journal of Molecular Structure. Roč. 1292, NOV (2023), č. článku 136099. ISSN 0022-2860. E-ISSN 1872-8014
Grant CEP: GA MŠMT(CZ) LTAUSA18016
Institucionální podpora: RVO:60077344
Klíčová slova: Cnucleoside * Oxadiazoles * Thiadiazoles * Antiviral * Antitumor * Heterocycles
Obor OECD: Microbiology
Impakt faktor: 3.8, rok: 2022
Způsob publikování: Open access
https://www.sciencedirect.com/science/article/pii/S0022286023011924?via%3Dihub

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.
Trvalý link: https://hdl.handle.net/11104/0345916