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【结 构 式】 
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【药物名称】Ranimustine, MCNU, NSC-270516, Cymerine 【化学名称】Methyl 6-[[[(2-chloroethyl)nitrosoamino]carbonyl]amino]-6-deoxy-alpha-D-glucopyranoside 【CA登记号】58994-96-0 【 分 子 式 】C10H18ClN3O7 【 分 子 量 】327.72386 |
【开发单位】Mitsubishi Pharma (Originator) 【药理作用】Oncolytic Drugs, DNA-Damaging Drugs |
合成路线1
1) By condensation of methyl 6-amino-6-deoxy-alpha-D-glucopyranoside (I) with 2-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (II) in THF / methanol. The 2-cyanophenyl ester analogue of compound (II) can also be used.
| 【1】 Kimura, G. (Tokyo Tanabe Co., Ltd.); Process for producing glucopyranose-nitrosourea cpds. and novel cpds. included therein. US 4156777 . |
| 【2】 Kimura, G.; Irie, K.; Kamibayashi, M.; Sekine, J.; Nagamatsu, T.; Ueno, S. (Tokyo Tanabe Co., Ltd.); Process for manufacturing chloroethylnitrosourea derivs. of alkylglucopyranose. JP 77151125; JP 804760 . |
| 【3】 Prous, J.; Castaner, J.; Ranimustine. Drugs Fut 1986, 11, 9, 762. |
合成路线2
2) The condensation of compound (I) with 2-chloroethyl isocyanate (III) by means of silver carbonate in acetonitrile water gives methyl 6-[[-(2-chloroethyl) amino]carbonylamino]-6-deoxy-alpha-D-glucopyranoside (IV), which is then nitrosated with NaNO2 in aqueous acetic acid
| 【1】 Kimura, G.; Sekine, J. (Tokyo Tanabe Co., Ltd.); Alkyl amino-glucopyranoside derivative and process for producing the same. CA 1044228; CH 610334; DE 2530416; FR 2276828; GB 1499760; JP 7606925; JP 77125126; JP 7797915; NL 7507973 . |
| 【2】 Prous, J.; Castaner, J.; Ranimustine. Drugs Fut 1986, 11, 9, 762. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 24328 | (2R,3S,4S,5R,6S)-2-(aminomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol | C7H15NO5 | 详情 | 详情 | |
| (III) | 11237 | 1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate | 1943-83-5 | C3H4ClNO | 详情 | 详情 |
| (IV) | 24332 | N-(2-chloroethyl)-N'-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl]methyl]urea | C10H19ClN2O6 | 详情 | 详情 |