11β-<2-(N,N-dimethylamino)ethoxy>estra-1,3,5(10)-triene-3,17β-diol | 130043-37-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11β-<2-(N,N-dimethylamino)ethoxy>estra-1,3,5(10)-triene-3,17β-diol
• 英文别名: (8S,9S,11S,13S,14S,17S)-11-[2-(dimethylamino)ethoxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 130043-37-7
• 化学式: C₂₂H₃₃NO₃
• 分子量: 359.509
• InChiKey: PVDWMCHTOGJGJJ-LLTZGFESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-benxyloxy-17,17-ethylenedioxyestra-1,3,5(10)-trien-11β-ol 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 17.58h， 生成 11β-<2-(N,N-dimethylamino)ethoxy>estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  Synthesis and biologic activities of 11β-substituted estradiol as potential antiestrogens

  摘要：

  The effect of attachment of a dimethylaminoethoxy or a dimethylaminopropoxy group at the 11 beta-position of estradiol (E2) on its relative binding affinity (RBA) to estrogen receptor (ER) and intrinsic biologic activity is described. The binding of 11 beta-[2-(N,N-dimethylamino) ethoxy]estra-1,3,5(10)-triene-3,17 beta-diol (4) and 11 beta-[3-(N,N- dimethylamino)propoxy]estra-1,3,5(10)-triene-3,17 beta-diol (5) to the ER from immature rat uterine tissue was measured relative to that of [3H]E2 by a competitive binding assay. It was found that the 11 beta-substituted E2 analogs have considerably lower RBA to ER than the corresponding parent compound. The intrinsic activity of compounds 4 and 5 were studied in terms of uterotrophic and antiuterotrophic activity. It was found that the uterotrophic activity of these compounds was drastically reduced compared with E2. However, no antiuterotrophic activity was observed in these compounds at dosages ranging from 1 to 100 micrograms/rat/d.

  DOI：

  10.1016/0039-128x(90)90022-4

文献信息

• Synthesis and biologic activities of 11β-substituted estradiol as potential antiestrogens
  作者：Xiaodong Qian、Yusuf J. Abul-Hajj

  DOI：10.1016/0039-128x(90)90022-4

  日期：1990.5

  The effect of attachment of a dimethylaminoethoxy or a dimethylaminopropoxy group at the 11 beta-position of estradiol (E2) on its relative binding affinity (RBA) to estrogen receptor (ER) and intrinsic biologic activity is described. The binding of 11 beta-[2-(N,N-dimethylamino) ethoxy]estra-1,3,5(10)-triene-3,17 beta-diol (4) and 11 beta-[3-(N,N- dimethylamino)propoxy]estra-1,3,5(10)-triene-3,17 beta-diol (5) to the ER from immature rat uterine tissue was measured relative to that of [3H]E2 by a competitive binding assay. It was found that the 11 beta-substituted E2 analogs have considerably lower RBA to ER than the corresponding parent compound. The intrinsic activity of compounds 4 and 5 were studied in terms of uterotrophic and antiuterotrophic activity. It was found that the uterotrophic activity of these compounds was drastically reduced compared with E2. However, no antiuterotrophic activity was observed in these compounds at dosages ranging from 1 to 100 micrograms/rat/d.