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【结 构 式】 
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【药物名称】 【化学名称】1,1'-(1,4-Phenylene)bis[2-[(3R,5aS,6R,8aS,9R,10R,12R,12aR)-3,6,9-trimethyl-3,12-epoxyperhydropyrano[4,3-j]-1,2-benzodioxepin-10-yl]ethanone] 【CA登记号】229981-82-2 【 分 子 式 】C40H54O10 【 分 子 量 】694.87038 |
【开发单位】Hauser (Originator), Johns Hopkins University (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Oncolytic Drugs, Treatment of Protozoal Diseases |
合成路线1
Reduction of artemisinin (I) by means of NaBH4 in THF/MeOH followed by treatment with BH3·H2O in MeOH yields (II). Finally, beta-artemether (II) is condensed with TMS-enol ether (IV) [obtained by protection of diacetylbenzene (III) by means of TMSOTf and Et3N in THF] in the presence of TiCl4 in CH2Cl2.
| 【1】 Posner, G.H.; Parker, M.H.; Ploypradith, P.; et al.; Antimalarial, antiproliferative, and antitumor activities of artemisinin-derived, chemically robust, trioxane dimers. J Med Chem 1999, 42, 21, 4275. |
| 【2】 Parker, M.H.; Shapiro, T.A.; Ploypradith, P.; Posner, G.H.; Northrup, J.; Daughenbaugh, R.J.; Woo, S.H.; Murray, C.; Elias, J.S.; Zheng, Q.Y. (Hauser, Inc.; Johns Hopkins University); C-10 carbon-substd. artemisinin-like trioxane cpds. having antimalarial, antiproliferative and antitumour activities. EP 1043988; WO 9933461 . |
| 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) | 22369 | Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one | 63968-64-9 | C15H22O5 | 详情 | 详情 |
| (II) | 31983 | (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane; methyl (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-10-yl ether | 71963-77-4 | C16H26O5 | 详情 | 详情 |
| (III) | 42273 | 1-(4-acetylphenyl)-1-ethanone | 1009-61-6 | C10H10O2 | 详情 | 详情 |
| (IV) | 42274 | trimethylsilyl 1-(4-[1-[(trimethylsilyl)oxy]vinyl]phenyl)vinyl ether; trimethyl[[1-(4-[1-[(trimethylsilyl)oxy]vinyl]phenyl)vinyl]oxy]silane | C16H26O2Si2 | 详情 | 详情 |
Extended Information