• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】1,1'-(1,4-Phenylene)bis[2-[(3R,5aS,6R,8aS,9R,10S,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 (diastereomer)

【 分 子 式 】C40H54O10

【 分 子 量 】694.87038

【开发单位】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) with NaBH4 at low temperature provided dihydroartemisinin (II), which was subsequently converted to the alpha-acetate (III) upon treatment with acetyl chloride in pyridine. The bis(trimethylsilyl) enol ether (V) - prepared by silylation of 1,4-diacetylbenzene (IV) with trimethylsilyl triflate - was then coupled to dihydroartemisinin acetate (III) in the presence of SnCl4 at -78 C to produce a diastereoisomeric mixture of adducts (VIa-c). The title alpha,alpha-dimer was then isolated as a minor component by means of preparative HPLC.

1 Borstnik, K.; Posner, G.H.; Paik, I.-H.; Dolan, P.; Kensler, T.W.; Xie, S.; Shapiro, T.A.; Northrop, J.; New chemical and biological aspects of artemisinin-derived trioxane dimers. Bioorg Med Chem 2002, 10, 1, 227.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIa) 56088 2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]-1-(4-{2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]acetyl}phenyl)-1-ethanone C40H54O10 详情 详情
(VIb) 56089 2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]-1-(4-{2-[(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]acetyl}phenyl)-1-ethanone C40H54O10 详情 详情
(VIc) 56090 2-[(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]-1-(4-{2-[(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]acetyl}phenyl)-1-ethanone C40H54O10 详情 详情
(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) 56087 (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 acetate C17H26O6 详情 详情
(IV) 42273 1-(4-acetylphenyl)-1-ethanone 1009-61-6 C10H10O2 详情 详情
(V) 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