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

【结 构 式】

【药物名称】Metahexestrol, NSC-297170, 3, 3'-HES

【化学名称】3,3'-Hexestrol
      meso-3,4-Bis(3'-hydroxyphenyl)hexane
      meso-3,3'-(1,2-Diethylethylene)diphenol

【CA登记号】71953-72-5

【 分 子 式 】C18H22O2

【 分 子 量 】270.37484

【开发单位】Universität Regensburg (Originator), AstraZeneca (Licensee)

【药理作用】ONCOLYTIC DRUGS

合成路线1

The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways: 1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al. -- yields preferably the cis-stilbene (II). Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III). 2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI), obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl, according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III). The meso-diastereomer (III) is separated by fractional crystallization from methanol. The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.

1 Hitova, M.; Kouzeva, V.; J Org Chem 1949, 14, Suppl. 1, 45-58.
2 Resende, C.; Barros, L.; Mota, A.; Barros, M.A.; Veloso, T.; Mesquita-Guimaraes, J.; Cunha, A.P.; J Cancer Res Clin Oncol 1982, 103, Suppl. 1, 165-180.
3 El-Ashmawi, N.; Abdel-Samad, Z.; Sallam, F.; Nassar, S.; Gamae, M.; Chem Lett 1973, 16, Suppl. 1, 1041-44.
4 Schonenberger, H.; Kranfelder, G.; Schmitt-Wallenborn, H. (Klinge Pharma GmbH); Novel di-(3'-hydroxyphenyl)-alkane cpds., process of preparation and their use in medicine. DE 2658307; US 4094994 .
5 Schonenberger, H.; Engel, J.; Hartmann, R.W.; Metahexestrol. Drugs Fut 1983, 8, 5, 413.
6 Picq, M.; et al.; Pentasubstituted quercetin analogues as selective inhibitors of particulate 3':5'-cyclic-AMP phosphodiesterase from rat brain. J Med Chem 1982, 24, 10, 1192-97.
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) 24239 bromo(ethyl)magnesium;ethylmagnesium bromide 925-90-6 C2H5BrMg 详情 详情
(IIIa) 36009 1-[(1S,2R)-1-ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene; 3-[(1R,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]phenyl methyl ether C20H26O2 详情 详情
(IIIb) 36010 3-[(1S,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]phenyl methyl ether; 1-[(1S,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene C20H26O2 详情 详情
(I) 36007 1-(3-methoxyphenyl)-1-propanone C10H12O2 详情 详情
(II) 36008 1-[(Z)-1-ethyl-2-(3-methoxyphenyl)-1-butenyl]-3-methoxybenzene; 3-[(Z)-1-ethyl-2-(3-methoxyphenyl)-1-butenyl]phenyl methyl ether C20H24O2 详情 详情
(V) 36012 1-(3-methoxyphenyl)-1-propanol C10H14O2 详情 详情
(VI) 36011 3-(1-chloropropyl)phenyl methyl ether; 1-(1-chloropropyl)-3-methoxybenzene C10H13ClO 详情 详情
Extended Information