Synthesis and antiviral evaluation of conformationally fixed bicyclohexanyl nucleosides with ethenyl group at C3'-position

Won Hee Kim; Kyung Ran Kim; Ah-Young Park; Hyung-Rock Lee; Jin-Ah Kang; Jang Ho Bae; Lak Shin Jeong; Hyung Ryong Moon

doi:10.1093/nass/nrn314

Synthesis and antiviral evaluation of conformationally fixed bicyclohexanyl nucleosides with ethenyl group at C3'-position

Nucleic Acids Symp Ser (Oxf). 2008:(52):621-2. doi: 10.1093/nass/nrn314.

Authors

Won Hee Kim¹, Kyung Ran Kim, Ah-Young Park, Hyung-Rock Lee, Jin-Ah Kang, Jang Ho Bae, Lak Shin Jeong, Hyung Ryong Moon

Affiliation

¹ College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan 609-735, Korea.

PMID: 18776533
DOI: 10.1093/nass/nrn314

Abstract

Conformationally fixed bicyclo[3.1.0]hexanyl nucleosides 1 and 2 with C3'-ethenyl group were successfully synthesized and evaluated against various viruses. Carbenoid intramolecular cycloaddition and diastereoselective Grignard reaction were employed as the key reaction steps.

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemical synthesis
Adenosine / chemistry
Adenosine / pharmacology
Antiviral Agents / chemical synthesis*
Antiviral Agents / chemistry
Antiviral Agents / pharmacology
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Bridged Bicyclo Compounds / pharmacology

Substances

Antiviral Agents
Bridged Bicyclo Compounds
Adenosine