Lithiation of Uracilnucleosides and its Application to the Synthesis of a New Class of Anti-HIV-1 Acyclonucleosides

Hiromichi Tanaka School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan

Masanori Baba Department of Bacteriology, Fukushima Medical College, Fukushima, 960-12, Japan

Hiroyuki Hayakawa School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan

Kazuhiro Haraguchi School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan

Tadashi Miyasaka School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan

Masaru Ubasawa Mitsubishi Kasei Corporation Research Center, 4Yokohama 227, Japan

Hideaki Takashima Mitsubishi Kasei Corporation Research Center, 4Yokohama 227, Japan

Kouichi Sekiya Mitsubishi Kasei Corporation Research Center, 4Yokohama 227, Japan

Issei Nitta Mitsubishi Kasei Corporation Research Center, 4Yokohama 227, Japan

Richard T. Walker Department of Chemistry, University of Birmingham, Birmingham, B15 2TT, United Kingdom

Erik De Clercq Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

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Abstract

A highly general and regioselective modification of the base moiety of uracilnucleosides can be accomplished based on lithiation chemistry. An application of this approach to the synthesis of various acyclouridine derivatives, in which both C-5 and C-6 positions were substituted, was carried out to improve the HIV-1 specific inhibitory activity of a new lead compound, l-[(2-hydroxyethoxy)methyl]-6-phenylthiothymine (HEPT).

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Lithiation of Uracilnucleosides and its Application to the Synthesis of a New Class of Anti-HIV-1 Acyclonucleosides

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Lithiation of Uracilnucleosides and its Application to the Synthesis of a New Class of Anti-HIV-1 Acyclonucleosides

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