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【结 构 式】

【药物名称】ST-789, PCF-39

【化学名称】N2-[5-(Hypoxanthin-9-yl)pentyloxycarbonyl]-L-arginine
      Nalpha-5-(1,6-Dihydro-6-oxo-9-purinyl)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
Extended Information