2-(3'-benzylideneacetyl)estradiol | 153760-05-5

• 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-(3'-benzylideneacetyl)estradiol
• 英文别名: 2-phenylacryloylestradiol
• CAS: 153760-05-5
• 化学式: C₂₇H₃₀O₃
• 分子量: 402.533
• InChiKey: QQTCYNFQONZOBX-VNPCZYLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(3'-benzylideneacetyl)estradiol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以60%的产率得到2'-phenylestradioldihydropyran-4'-one
  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：

  雌二醇 在 吡啶 、 氯化锆(IV) 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 2-(3'-benzylideneacetyl)estradiol
  参考文献：
  名称：

  以雌甾为母核的2位或16位取代的查耳酮衍生 物及其制备方法和用途

  摘要：

  本发明属药物化学领域，涉及以雌甾为母核的2位或16位取代的查耳酮衍生物及其制备方法和应用。其制备方法是将查尔酮结构片段骈和在雌甾母体上，保持或增强了抗肿瘤细胞的活性及抑制肿瘤细胞血管生成的活性。具有如下结构通式：通式Ⅰ通式Ⅱ经体外抗肿瘤细胞增殖活性试验和鸡胚尿囊膜试验研究证明：该类衍生物具有一定的抗肿瘤细胞增殖活性和抑制肿瘤细胞血管生成的活性，在量效关系研究中，其对肿瘤细胞的抑制作用优于具有广谱抗肿瘤活性的2‑甲氧基雌二醇，且半衰期延长。

  公开号：

  CN105153259B