3'-formylestradiolchromone 17β-acetate | 153759-93-4

• 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: 3'-formylestradiolchromone 17β-acetate
• 英文别名: [(2S,5S,6S,9S,10R)-18-formyl-5-methyl-19-oxo-16-oxapentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(21),13,15(20),17-tetraen-6-yl] acetate
• CAS: 153759-93-4
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: IMUFIUYWVYCXBD-JSYOHWIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  4-环己基-3-硫代氨基脲 、 3'-formylestradiolchromone 17β-acetate 在 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以65%的产率得到
  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 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以64%的产率得到3'-formylestradiolchromone 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, binding affinities and uterotrophic activity of some 2-substituted estradiol and ring-A-fused pyrone derivatives
  作者：AMME Omar、IC Ahmed、OM AboulWafa、AM Hassan、KA Ismail、MMM El-Din、NA Mansour

  DOI：10.1016/0223-5234(94)90122-8

  日期：1994.1

  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.