Publication details
Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity
| Authors | |
|---|---|
| Year of publication | 2023 |
| Type | Article in Periodical |
| Magazine / Source | Journal of Molecular Structure |
| MU Faculty or unit | |
| Citation | |
| Web | https://doi.org/10.1016/j.molstruc.2023.136099 |
| Doi | http://dx.doi.org/10.1016/j.molstruc.2023.136099 |
| Keywords | C -nucleoside; Oxadiazoles; Thiadiazoles; Antiviral; Antitumor; Heterocycles |
| 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 & 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. |