4 '-Selenonucleosides: Regio- and Stereoselective Synthesis of Novel Ribavirin and Acadesine Analogs as Anti-Hepatitis C Virus (HCV) Agents
  • Lee, Hyejin
  • Jarhad, Dnyandev B.
  • Lee, Ahrim
  • Lee, Choongho
  • Jeong, Lak Shin
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초록

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.

키워드

2′-C-methyl-4′-seleno-ribavirin and -acadesineBioisotereHepatitis C virusVorbrüggen condensationX-ray crystallographyACTIVATED PROTEIN-KINASETREATMENT-NAIVE PATIENTSINTERFERON-ALPHA 2APLUS RIBAVIRINANTIVIRAL ACTIVITYAICA-RIBOSIDE1ST SYNTHESISDOUBLE-BLINDIN-VITROMECHANISM
제목
4 '-Selenonucleosides: Regio- and Stereoselective Synthesis of Novel Ribavirin and Acadesine Analogs as Anti-Hepatitis C Virus (HCV) Agents
저자
Lee, HyejinJarhad, Dnyandev B.Lee, AhrimLee, ChoonghoJeong, Lak Shin
DOI
10.1002/ajoc.202100563
발행일
2021-11
유형
Article
저널명
Asian Journal of Organic Chemistry
10
11
페이지
2993 ~ 2999