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【结 构 式】 
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【药物名称】MHP-46 【化学名称】(3R,5aS,6R,8aS,9R,10R,12S,12aR)-Octahydro-3,6,9-trimethyl-10-(2-furyl)-3,12-epoxy-12H-pyrano[4,3-j][1,2]benzodioxepin 【CA登记号】204503-68-4 【 分 子 式 】C19H26O5 【 分 子 量 】334.41607 |
【开发单位】Johns Hopkins University (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases |
合成路线1
Artemisinin (I) was reduced to the dihydro analogue (II), and subsequently the 10-hydroxyl group was substituted for a fluorine atom using diethylaminosulfur trifluoride. The desired 10-beta-isomer (III) was then separated by column chromatography. Finally, boron trifluoride-promoted Friedel Crafts condensation with furan (IV) at low temperature provided the target furyl compound, the major 10-beta isomer being isolated by chromatography on Florisil.
| 【1】 Posner, G.H.; Parker, M.H.; Northrop, J.; Elias, J.S.; Ploypradith, P.; Xie, S.; Shapiro, T.A.; Orally active, hydrolytically stable, semisynthetic, antimalarial trioxanes in the artemisinin family. J Med Chem 1999, 42, 2, 300. |
| 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) | 22370 | Dihydroartemisinin; (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-ol | C15H24O5 | 详情 | 详情 | |
| (III) | 22371 | (1R,4S,5R,8S,9R,10R,12S,13R)-10-fluoro-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane | C15H23FO4 | 详情 | 详情 | |
| (IV) | 22372 | Furan | 110-00-9 | C4H4O | 详情 | 详情 |