2-acetylestradiol-3-benzoate 17β-acetate | 161553-37-3

• 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: 2-acetylestradiol-3-benzoate 17β-acetate
• 英文别名: [(8R,9S,13S,14S,17S)-2-acetyl-17-acetyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 161553-37-3
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: KWGMIEWIPWYVON-OXIGCPNHSA-N

物化性质

• 沸点：
  617.1±55.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetylestradiol-3-benzoate 17β-acetate 在 吡啶 、 氢氧化钾 作用下， 反应 1.0h， 以80%的产率得到2-benzoylacetylestradiol 17β-acetate
  参考文献：
  名称：

  Synthesis, binding affinities and uterotrophic activity of some 2-substituted estradiol and ring-A-fused pyrone derivatives

  摘要：

  A series of estradiol analogs has been synthesized and examined as potential estrogens. Nuclear modifications included a variety of substituents at the 2 position of estradiol, which was previously thought to be inhibitory for activity, and inclusion of the 3-phenolic hydroxyl group in a gamma-pyrone and 3'-formylchromone rings fused to ring A of estradiol. The estrogen relative binding affinities and in vivo assays for uterotrophic activity in rats showed that all the tested compounds were capable of displacing [H-3]E(2) from the estrogen receptor sites by different degrees. The highest inhibition of [H-3]E(2) binding (78%) to the estrogen receptor was displayed by 2-acetylestradiol which was also a potent uterotrophic agent. Omission of the free 3-hydroxyl functionality by inclusion in a gamma-pyrone ring produced a chromone derivative that was capable of inhibiting [3H]E(2), binding by 60% and displayed a uterotrophic response of 97%. Further nuclear modification by introduction of thiosemicarbazone moieties decreased the uterotrophic activity, the highest activity being elicited by the p-bromophenyl thiosemicarbazone derivative. The diketone 2-benzoylacetylestradiol 17 beta-acetate, 2-(3'-benzylideneacetyl)estradiol and 2-[3'-(3-anisylidene)acetyl]estradiol exhibited high inhibition of binding affinity while eliciting approximate to 50% the uterotrophic activity of estradiol.

  DOI：

  10.1016/0223-5234(94)90122-8
• 作为产物：
  描述：

  2-acetylestradiol 17β-acetate 、 苯甲酰氯 在 吡啶 作用下， 反应 14.0h， 以79%的产率得到2-acetylestradiol-3-benzoate 17β-acetate
  参考文献：
  名称：

  Synthesis, binding affinities and uterotrophic activity of some 2-substituted estradiol and ring-A-fused pyrone derivatives

  摘要：

  A series of estradiol analogs has been synthesized and examined as potential estrogens. Nuclear modifications included a variety of substituents at the 2 position of estradiol, which was previously thought to be inhibitory for activity, and inclusion of the 3-phenolic hydroxyl group in a gamma-pyrone and 3'-formylchromone rings fused to ring A of estradiol. The estrogen relative binding affinities and in vivo assays for uterotrophic activity in rats showed that all the tested compounds were capable of displacing [H-3]E(2) from the estrogen receptor sites by different degrees. The highest inhibition of [H-3]E(2) binding (78%) to the estrogen receptor was displayed by 2-acetylestradiol which was also a potent uterotrophic agent. Omission of the free 3-hydroxyl functionality by inclusion in a gamma-pyrone ring produced a chromone derivative that was capable of inhibiting [3H]E(2), binding by 60% and displayed a uterotrophic response of 97%. Further nuclear modification by introduction of thiosemicarbazone moieties decreased the uterotrophic activity, the highest activity being elicited by the p-bromophenyl thiosemicarbazone derivative. The diketone 2-benzoylacetylestradiol 17 beta-acetate, 2-(3'-benzylideneacetyl)estradiol and 2-[3'-(3-anisylidene)acetyl]estradiol exhibited high inhibition of binding affinity while eliciting approximate to 50% the uterotrophic activity of estradiol.

  DOI：

  10.1016/0223-5234(94)90122-8