4′‐Selenonucleosides: Regio‐ and Stereoselective Synthesis of Novel Ribavirin and Acadesine Analogs as Anti‐Hepatitis C Virus (HCV) Agents. Issue 11 (1st October 2021)

• Record Type: Journal Article
• Authors: Lee, Hyejin; Jarhad, Dnyandev B.; Lee, Ahrim; Lee, Choongho; Jeong, Lak Shin
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 11(2021)
• Page Start: 2993
• Page End: 2999
• Publication Date: 2021-10-01
• Subjects: Bioisotere -- 2′-C-methyl-4′-seleno-ribavirin and -acadesine -- Hepatitis C virus -- Vorbrüggen condensation -- X-ray crystallography; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100563
• Languages: English
• ISSNs: 2193-5807

Abstract

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 N 3−C2 bond of a purine by ethylenediamine (EDA) as the key step. Abstract : Based on the bioisosteric rationale between oxygen and selenium, we herein report a regio‐ and stereoselective synthesis of the 2′‐C‐methyl‐4′‐seleno‐ribavirin and ‐acadesine as potential anti‐HCV agents.