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Paper | Regular issue | Vol 100, No. 10, 2020, pp.1599-1612
Published online, 4th August, 2020
DOI: 10.3987/COM-20-14312
Design and Synthesis of 4'-Cyano Dideoxy Isonucleosides and Their Activity against HIV-1 and HBV

Kengo Onitsuka, Kakeru Yamaguchi, Ryoh Tokuda, Nobuyo Higashi-Kuwata, Shunsuke Kuwahara, Hiroki Kumamoto, Kenji Maeda, Kazuhiro Haraguchi, Hiroaki Mitsuya, and Shuhei Imoto*

*Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan

Abstract

Nucleoside reverse-transcriptase inhibitors are major antiviral agents against HIV-1 and HBV. Here, we describe the synthesis of a novel 4'-cyano dideoxy isonucleoside 6 and its phosphoramidate prodrug 7. Intermediate 16 is a promising precursor for the preparation of isonucleosides bearing substituents at the 4' position with various nucleobases. In addition, 6 and 7 were evaluated for their antiviral properties against HIV-1 and HBV. Compound 7 displayed weak anti-HIV activity (EC50 = 61.4 μM) and had no observed cytotoxicity in two different cell systems.