New Neplanocin Analogues II. Enzymatic One-Step Synthesis and Antitumor Activity of 6′-(3-sn-Phosphatidyl)Neplanocin a Derivatives

Satoshi Shuto Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Hiromichi Ito Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Takumi Obara Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Keiji Nakagami Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Masao Yaso Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Satoshi Yaginuma Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Masatoshi Tsujino Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Tetsu Saito Research Laboratories, Toyo Jozo Co., Ltd., 632-1 Mifuku, Ohito-cho, Tagata-gun, Shizuoka, 410-23, Japan

Akira Matsuda Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo, 060, Japan

Tohru Ueda Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo, 060, Japan

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Abstract

A novel series of neplanocin analogues, 6′-(3-sn-phosphatidyl)neplanocin As bearing a variety of fatty acyl or alkyl residues in the glyceride moiety (2b-2h), were synthesized by means of phospholipase D-catalyzed transphosphatidylation. Among them, 2b, 2c, and 2e each exhibited significant antitumor effect against P388 leukemia in mice, which evidently surpassed that of parent compound neplanocin A.

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New Neplanocin Analogues II. Enzymatic One-Step Synthesis and Antitumor Activity of 6′-(3-sn-Phosphatidyl)Neplanocin a Derivatives

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New Neplanocin Analogues II. Enzymatic One-Step Synthesis and Antitumor Activity of 6′-(3-sn-Phosphatidyl)Neplanocin a Derivatives

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