Abstract
Intrigued by the biological activity of 2′-C-methylribofuranosyl nucleosides, and ribavirin/acadesine, based on the bioisosteric rationale between oxygen and selenium, we herein report a design and synthesis of the 2′-C-methyl-4′-seleno-ribavirin and -acadesine as potential anti-HCV agents. The 2′-C-methyl 4′-selenoribavirin was synthesized in a regio- and stereoselective manner and completely characterized through 2D NMR and X-ray crystallography. While the 2′-C-methyl 4′-selenoacadesine has been efficiently synthesized by utilizing purine-ring opening/degradation procedure via nucleophilic cleavage of N3−C2 bond of a purine by ethylenediamine (EDA) as the key step.
Original language | English |
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Pages (from-to) | 2993-2999 |
Number of pages | 7 |
Journal | Asian Journal of Organic Chemistry |
Volume | 10 |
Issue number | 11 |
DOIs | |
State | Published - Nov 2021 |
Keywords
- 2′-C-methyl-4′-seleno-ribavirin and -acadesine
- Bioisotere
- Hepatitis C virus
- Vorbrüggen condensation
- X-ray crystallography