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【结 构 式】 
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【药物名称】SM-295072 【化学名称】6-Amino-9-benzyl-2-(2-hydroxyethylsulfanyl)-9H-purin-8-ol 【CA登记号】226907-03-5 (tautomer) 【 分 子 式 】C14H15N5O2S 【 分 子 量 】317.37195 |
【开发单位】Japan Energy (Originator), Sumitomo Pharmaceuticals (Originator) 【药理作用】IMMUNOMODULATING AGENTS, Immunostimulants, Oncolytic Drugs, IL-4 Production Inhibitors, Interferon Inducers |
合成路线1
Condensation between aminomalononitrile (I) and benzyl isocyanate (II) produces imidazole (III). This is then cyclized with benzoyl isothiocyanate (IV) in the presence of NaOH to furnish the mercaptopurine derivative (V). Finally, alkylation of thiol (V) with 2-bromoethanol (VI) gives rise to the target hydroxyethyl sulfide.
| 【1】 Kawakami, H.; Ogino, T.; Kurimoto, A. (Japan Energy Corp.; Sumitomo Pharmaceuticals Co., Ltd.); Novel heterocyclic cpds.. EP 1035123; US 6329381; WO 9928321 . |
| 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) | 63650 | 2-aminomalononitrile | C3H3N3 | 详情 | 详情 | |
| (II) | 16730 | 1-(Isocyanatomethyl)benzene; Benzyl Isocyanate | 3173-56-6 | C8H7NO | 详情 | 详情 |
| (III) | 63651 | 5-amino-1-benzyl-2-hydroxy-1H-imidazole-4-carbonitrile | C11H10N4O | 详情 | 详情 | |
| (IV) | 23530 | benzoyl isothiocyanate | 532-55-8 | C8H5NOS | 详情 | 详情 |
| (V) | 63652 | 6-amino-9-benzyl-2-sulfanyl-9H-purin-8-ol | C12H11N5OS | 详情 | 详情 | |
| (VI) | 10059 | Ethylene bromohydrin; 2-Bromo-1-ethanol | 540-51-2 | C2H5BrO | 详情 | 详情 |
Extended Information