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【结 构 式】

【药物名称】Sobuzoxane, MST-16, Perazolin

【化学名称】4,4'-Ethane-1,2-diylbis[1-(isobutoxycarbonyloxymethyl)piperazine-2,6-dione]

【CA登记号】98631-95-9

【 分 子 式 】C22H34N4O10

【 分 子 量 】514.53708

【开发单位】Shanghai Institute Materia Medica (Originator), Zenyaku Kogyo (Originator)

【药理作用】ONCOLYTIC DRUGS, DNA Topoisomerase II Inhibitors, DNA-Intercalating Drugs

合成路线1

4,4'-Ethane-1,2-diylbis(piperazine-2,6-dione) in DMF is heated at 130 C for 10 min. Aqueous formaldehyde is then gradually added, and the mixture is heated at 130 C for 1.5 h. 4,4'-Ethane-1,2-diylbis[1-(hydroxymethyl)piperazine-2,6-dione] precipitates from the solution on cooling. It can be purified by recrystallization from dioxane. The hydroxymethyl compound (II) is then stirred with pyridine and chloroform at 10 C. Isobutoxycarbonyl chloride is gradually added, and the mixture is stirred for 6 h at room temperature. The resulting solution is diluted with chloroform. The combined solution is washed with water and then dried. Evaporation of the chloroform gives MST-16. It can be purified by recrystallization from ethylene glycol monomethyl ether.

1 Ruyun, J.; MST-16. Drugs Fut 1986, 11, 4, 267.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 13423 1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate 543-27-1 C5H9ClO2 详情 详情
(I) 28033 4-[2-(3,5-dioxo-1-piperazinyl)ethyl]-2,6-piperazinedione C10H14N4O4 详情 详情
(II) 28034 1-(hydroxymethyl)-4-[2-[4-(hydroxymethyl)-3,5-dioxo-1-piperazinyl]ethyl]-2,6-piperazinedione C12H18N4O6 详情 详情
Extended Information