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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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4초록
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 -acadesine; Bioisotere; Hepatitis C virus; Vorbrüggen condensation; X-ray crystallography; ACTIVATED PROTEIN-KINASE; TREATMENT-NAIVE PATIENTS; INTERFERON-ALPHA 2A; PLUS RIBAVIRIN; ANTIVIRAL ACTIVITY; AICA-RIBOSIDE; 1ST SYNTHESIS; DOUBLE-BLIND; IN-VITRO; MECHANISM
- 제목
- 4 '-Selenonucleosides: Regio- and Stereoselective Synthesis of Novel Ribavirin and Acadesine Analogs as Anti-Hepatitis C Virus (HCV) Agents
- 저자
- Lee, Hyejin; Jarhad, Dnyandev B.; Lee, Ahrim; Lee, Choongho; Jeong, Lak Shin
- 발행일
- 2021-11
- 유형
- Article
- 권
- 10
- 호
- 11
- 페이지
- 2993 ~ 2999