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【结 构 式】 
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【药物名称】Spirohydantoin mustard(former USAN), Spiromustine, SHM, NSC-172112, Speratine 【化学名称】3-[2-[Bis(2-chloroethyl)amino]ethyl]-1,3-diazaspiro[4,5]decane-2,4-dione 【CA登记号】56605-16-4 【 分 子 式 】C14H23Cl2N3O2 【 分 子 量 】336.26431 |
【开发单位】National Cancer Institute (Originator), Roberts (Licensee) 【药理作用】ONCOLYTIC DRUGS, DNA-Damaging Drugs |
合成路线1
The alkylation of 5,5-pentamethylenehydantoin (I) with 1-bromo-2-chloroethane (II) by means of KOH in refluxing ethanol gives 3-(2-chloroethyl)-5,5-pentamethylenehydantoin (II), which is condensed with diethanolamine (IV) by means of NaI in hot DMF yielding 3-[2-[bis(2 hydroxyethyl)amino]ethyl] 5,5-pentamethylenehydantoin (V) Finally, this compound is treated with hot POCl3.
| 【1】 Peng, G.W.; et al.; Potential central nervous system antitumor agents. Hydantoin derivatives. J Med Chem 1975, 18, 8, 846. |
| 【2】 Prous, J.; Castaner, J.; Spiromustine. Drugs Fut 1986, 11, 9, 773. |
| 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) | 24270 | 1,3-diazaspiro[4.5]decane-2,4-dione | 702-62-5 | C8H12N2O2 | 详情 | 详情 |
| (II) | 24271 | 1-bromo-2-chloroethane | 107-04-0 | C2H4BrCl | 详情 | 详情 |
| (III) | 24272 | 3-(2-chloroethyl)-1,3-diazaspiro[4.5]decane-2,4-dione | C10H15ClN2O2 | 详情 | 详情 | |
| (IV) | 24273 | 2-[(2-hydroxyethyl)amino]-1-ethanol | 111-42-2 | C4H11NO2 | 详情 | 详情 |
| (V) | 24274 | 3-[2-[bis(2-hydroxyethyl)amino]ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione | C14H25N3O4 | 详情 | 详情 |