Synthesis and Evaluation of Water-Soluble Non-Prodrug Analogs of Docetaxel Bearing sec-Aminoethyl Group at the C-10 Position
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概要
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To develop non-prodrugs of taxoids with satisfactory stability in vivo, high water-solubility, and potent antitumor activity, we prepared several 10-O-sec-aminoethyl decetaxel analogs (3) and evaluated their cytotoxicity against mouse leukemia and human tumor cell lines, microtubule disassembly-inhibitory activity, and water-solubility. These analogs were synthesized from the 10-O-allyl baccatin derivatives (5a-c) using the β-lactam synthon method. Among these analogs, the 10-O-(2-morpholinoethyl) (18,21) and 10-O-(2-thiomorpholinoethyl) (19,24) analogs exhibited cytotoxicity comparable or superior to that of docetaxel (2). In addition, the methanesulfonic acid salt (18a) had a high water-solubility.
- 1998-05-15
著者
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HIROTA Yasuhide
New Product Research Laboratories III R&D Division, Daiichi Pharmaceutical Company Ltd.
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HIROTA Yukiko
Sagami Chemical Research Center
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Hirota Y
Sagami Chemical Research Center
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Ishii M
Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University
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Mitsui Ikuo
New Product Research Laboratories Iv Daiichi Pharmaceitucal Co. Ltd.
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Uoto K
Medicinal Chemistry Research Laboratory Daiichi Pharmaceutical Co. Ltd. Tokyo R&d Center
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Terasawa H
Medicinal Chemistry Research Laboratory Daiichi Pharmaceutical Co. Ltd. Tokyo R&d Center
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Hirota Yasuhide
New Product Research Laboratories Iii R&d Division Daiichi Pharmaceutical Company Ltd.
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Soga T
Medicinal Chemistry Research Laboratory Daiichi Pharmaceutical Co. Ltd. Tokyo R&d Center
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UOTO Kouichi
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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TAKENOSHITA Haruhiro
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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YOSHINO Toshiharu
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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ANDO Shuichi
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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TERASAWA Hirofumi
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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SOGA Tsunehiko
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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Ando Shuichi
New Product Research Laboratories Iv Daiichi Pharmaceitucal Co. Ltd.
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Yoshino Toshiharu
Medicinal Chemistry Research Laboratory Daiichi Pharmaceutical Co. Ltd. Tokyo R&d Center
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Takenoshita Haruhiko
New Product Research Laboratories IV, Daiichi pharmaceitucal Co., Ltd.,
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