2-benzoylacetylestradiol 17β-acetate | 153760-00-0

• 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-benzoylacetylestradiol 17β-acetate
• 英文别名: 2-benzoylacetylestradiol-17β-acetate；[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-2-(3-oxo-3-phenylpropanoyl)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 153760-00-0
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: PFHCOGHHBHSUDE-VOLKQVRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzoylacetylestradiol 17β-acetate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以53%的产率得到2-(3'-phenylpyrazol-5'yl)estradiol 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 在 吡啶 、 氢氧化钾 作用下， 反应 15.0h， 生成 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

文献信息

• Synthesis and biological evaluation of some novel 2-(pyrimidin-4-yl)estradiol derivatives
  作者：KA Ismail、AA El-Tombary、AMME Omar、OM Abouwafa、NI Madi

  DOI：10.1016/0223-5234(96)88252-3

  日期：1995.1

  The preparation and characterization of some novel 2-(pyrimidin-4-yl)estradiol derivatives are presented. The synthesis was achieved by the reaction of 2-benzoylacetylestradiol 17 beta-acetate with guanidines, urea, thiourea and a variety of thiourea derivatives according to the Traube synthesis. The synthesized compounds were evaluated for their uterotrophic and antifertility activities in mature female albino rats. All compounds showed relatively moderate uterotrophic activity (55-73%) based on dry uterine weight gain. The antifertility activity, as assessed by the post-coital antiimplantation activity test, was also of moderate potency for most compounds. However, 2-(1-p-bromophenyl-2(1H)-thioxb-6-phenylpyrimidin-4-yl)estradiol 8 displayed excellent antiimplantation activity (100%), and was equipotent to estradiol as an antifertility agent; 8 prevented implantation completely in rats at a dose of 0.035 mg/kg body weight.