【结 构 式】 |
【药物名称】ST-789, PCF-39 【化学名称】N2-[5-(Hypoxanthin-9-yl)pentyloxycarbonyl]-L-arginine 【CA登记号】104317-64-8 【 分 子 式 】C17H26N8O5 【 分 子 量 】422.44737 |
【开发单位】Gaslini Univ. (Originator), Sigma-Tau (Originator) 【药理作用】IMMUNOMODULATING AGENTS, Immunomodulators |
合成路线1
The reaction of 4,6-dichloropyrimidin-5-amine (I) with 5-aminopentanol (I) gives 4-chloro-6-(5-hydroxypentylamino)pyrimidin-5 amine (III), which is cyclized with triethyl orthoformate (IV) yielding 6-chloro-9-(5-hydroxypentyl)purine (V). The hydrolysis of (V) with formic acid affords 9-(5-hydroxypentyl) hypoxanthine (VI), which is treated with phosgene (VII) to give 9-[5-(chlorocarbonyloxy)pentyl]hypoxanthine (VIII). Finally, this compound is condensed with arginine (IX).
【1】 Stradi, R.; Cornaglia-Ferraris, P.; Perezzani, L.S.; Forni, G.; Riccardi, C.; PCF-39. Drugs Fut 1987, 12, 2, 134. |
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) | 22845 | 5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine | 5413-85-4 | C4H3Cl2N3 | 详情 | 详情 |
(II) | 22846 | 5-amino-1-pentanol | 2508-29-4 | C5H13NO | 详情 | 详情 |
(III) | 22847 | 5-[(5-amino-6-chloro-4-pyrimidinyl)amino]-1-pentanol | C9H15ClN4O | 详情 | 详情 | |
(IV) | 21304 | Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether | 122-51-0 | C7H16O3 | 详情 | 详情 |
(V) | 22849 | 5-(6-chloro-9H-purin-9-yl)-1-pentanol | C10H13ClN4O | 详情 | 详情 | |
(VI) | 22850 | 9-(5-hydroxypentyl)-9H-purin-6-ol | C10H14N4O2 | 详情 | 详情 | |
(VIII) | 22852 | 9-[5-[(chlorocarbonyl)oxy]pentyl]-6-hydroxy-9H-purine | C11H13ClN4O3 | 详情 | 详情 | |
(IX) | 22853 | Arginine; 2-Amino-5-guanidinopentanoic acid | C6H14N4O2 | 详情 | 详情 |