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【结 构 式】 
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【药物名称】Cystemustine, CMSO2EN2 【化学名称】N-(2-Chloroethyl)-N'-[2-(methylsulfonyl)ethyl]-N-nitrosourea 【CA登记号】79955-36-5 【 分 子 式 】C6H12ClN3O4S 【 分 子 量 】257.69724 |
【开发单位】CNRS (Originator), INSERM (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA-Damaging Drugs |
合成路线1
The reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III), which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV). The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI), which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.
| 【1】 Godeneche, D.; Imbach, J.-L.; Madelmont, J.-C.; Meyniel, G.; Moreau, M.-F.; Oiry, J.; Parry, D. (CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale)); Novel nitrosourea cpds. Process of preparation. Compsns. based on these cpds. useful in anticancer chemotherapy. EP 0185020; FR 2562890; JP 1988502269; WO 8504655 . |
| 【2】 Madelmont, J.-C.; Godeneche, D.; Moreau, M.-F.; Parry, D.; Meyniel, G.; Oiry, J.; Imbach, J.-L. (CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale)); Nitrosoureas compounds, preparation thereof and utilization thereof in anticancerous. US 5001158 . |
| 【3】 Meyniel, G.; Duprat, J.; Mathe, G.; Plagne, R.; Godeneche, D.; Parry, D.; Madelmont, J.C.; Chabard, J.L.; New cysteamin(2-chloroethyl)nitrosoureas. Synthesis and preliminary antitumor results. J Med Chem 1985, 28, 9, 1346-50. |
| 【4】 Madelmont, J.C.; Cystemustine. Drugs Fut 1994, 19, 1, 27. |
| 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) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (II) | 11237 | 1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate | 1943-83-5 | C3H4ClNO | 详情 | 详情 |
| (III) | 11238 | 4-nitrophenyl N-(2-chloroethyl)carbamate | C9H9ClN2O4 | 详情 | 详情 | |
| (IV) | 11239 | 4-nitrophenyl 1-(2-chloroethyl)-2-oxo-1-hydrazinecarboxylate | C9H8ClN3O5 | 详情 | 详情 | |
| (V) | 11240 | 2-(Methylsulfanyl)ethylamine; 2-(Methylthio)ethylamine; 2-(Methylsulfanyl)-1-ethanamine | 18542-42-2 | C3H9NS | 详情 | 详情 |
| (VI) | 11241 | 1-(2-Chloroethyl)-N-[2-(methylsulfanyl)ethyl]-2-oxo-1-hydrazinecarboxamide | C6H12ClN3O2S | 详情 | 详情 |
Extended Information