A New Class of Nitrosoureas. IX. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-6-yl or methyl 2-acetamido-2-deoxy-α-D-glucopyranosid-6-yl)-1-nitrosoureas
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概要
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A series of eight 3,3-disubstituted nitrosoureas (IVa-h) having the nitrosoureido group at the C-6 position of methyl glucopyranoside or methyl 2-acetamido-2-deoxy-glucopyranoside was prepared and tested for antitumor activities. Heating of the 6-O-p-tolylsulfonyl derivatives (I and II) with various alkylamines followed by reaction with 2-chloroethyl isocyanate gave the corresponding ureas (IIIa-h), which were nitrosated with nitrogen tetroxide to give IVa-h in high yields. The nitrosoureas (IVa-h) were significantly less active than the other positional isomers with respect to the nitrosoureido group prepared previously. Compounds IVa-h appear to be activated by a γ hydroxyl group at the C-4 position. The rate of activation, however, proved to be much slower than those of the C-1 or C-3 positional isomers having a β hydroxyl group. The structure-activity relationships of the positional isomers are discussed in the light of this difference in the rate of activation.
- 1983-11-25
著者
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武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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森川 民雄
Organic Chemistry Research Laboratory
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辻原 健二
Research Laboratories, Tanabe Seiyaku Co., Ltd.
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森川 民雄
Research Laboratories, Tanabe Seiyaku Co., Ltd.
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新井 淑久
Research Laboratories, Tanabe Seiyaku Co., Ltd.
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武田 幹男
Research Laboratories, Tanabe Seiyaku, Co., Ltd.
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武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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新井 淑久
Research Laboratories Tanabe Seiyaku Co. Ltd.
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辻原 健二
Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.
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辻原 健二
Research Laboratories Tanabe Seiyaku Co. Ltd.
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