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Nucleosides, Nucleotides & Nucleic Acids Volume 34, 2015 - Issue 8
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Original Articles

Design, Synthesis, and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir: Exomethylene Acycloguanine Nucleosides and Their Monophosphate Derivatives

Shuhei ImotoFaculty of Pharmaceutical Sciences, Sojo University, Nishi-ku, Kumamoto, Japan
,
Satoru KohgoDepartment of Pharmaceutical Sciences, Nihon Pharmaceutical University, Inamachi, Kita-adachi-gun, Saitama, Japan;Center for Clinical Sciences, National Center for Global Health and Medicine, Shinju-ku, Tokyo, Japan
,
Ryoh TokudaFaculty of Pharmaceutical Sciences, Sojo University, Nishi-ku, Kumamoto, Japan
,
Hiroki KumamotoSchool of Pharmacy, Showa University, Shinagawa-ku, Tokyo, Japan
,
Manabu AokiDepartment of Medical Technology, Kumamoto Health Science University, Kumamoto, Japan
,
Masayuki AmanoDepartments of Infectious Diseases and Hematology, Kumamoto University School of Medicine, Kumamoto, Japan
,
Nobuyo Kuwata-HigashiDepartments of Infectious Diseases and Hematology, Kumamoto University School of Medicine, Kumamoto, Japan
,
Hiroaki MitsuyaCenter for Clinical Sciences, National Center for Global Health and Medicine, Shinju-ku, Tokyo, Japan;Departments of Infectious Diseases and Hematology, Kumamoto University School of Medicine, Kumamoto, Japan;Experimental Retrovirology Section, HIV and AIDS Malignancy Branch, National Cancer Institute, National Institutes of Health, Bethesda, Maryland, USA
&
Kazuhiro HaraguchiDepartment of Pharmaceutical Sciences, Nihon Pharmaceutical University, Inamachi, Kita-adachi-gun, Saitama, JapanCorrespondence[email protected]
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Pages 590-602 | Received 14 Jan 2015, Accepted 31 Mar 2015, Published online: 13 Jul 2015
 
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Abstract

Exomethylene acycloguanine nucleosides 4, 6 and its monophosphate derivatives 5, 7, and 8 have been synthesized. Mitsunobu-type coupling of 2-N-acetyl-6-O-diphenylcarbamoylguanine (11) with primary alcohols proceeded regioselectively to furnish the desired N9-substituted products in moderate yield. Evaluation of 4-8 for anti-HBV activity in HepG2 cells revealed that the phosphonate derivative 8 was found to exhibit moderated activity (EC50 value of 0.29 μM), but cytotoxicity (CC50 value of 39 μM) against the host cells was also observed.

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