Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

Yuichi Yoshimura Research & Development Division, Yamasa Corporation, 2-10-1 Araoicho, Choshi, Chiba, 288, Japan

Fumitaka Kano Research & Development Division, Yamasa Corporation, 2-10-1 Araoicho, Choshi, Chiba, 288, Japan

Shuichi Miyazaki Research & Development Division, Yamasa Corporation, 2-10-1 Araoicho, Choshi, Chiba, 288, Japan

Noriyuki Ashida Research & Development Division, Yamasa Corporation, 2-10-1 Araoicho, Choshi, Chiba, 288, Japan

Shinji Sakata Research & Development Division, Yamasa Corporation, 2-10-1 Araoicho, Choshi, Chiba, 288, Japan

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

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

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

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

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Abstract

2′-Deoxy-, 2′-bromo-, and arabino-1′-C-cyano-pyrimidine nucleosides were synthesized from O² ,2′-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1′,2′-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed.

^†This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday.

Notes

^†This paper is dedicated to Dr. Yoshihisa Mizuno on the occasion of his 75th birthday.

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Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

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Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

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