4-(1-(4-(2-hydroxyethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol | 110025-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(1-(4-(2-hydroxyethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
• 英文别名: 4-{1-[4-(2-Hydroxyethoxy)phenyl]-2-phenylbut-1-en-1-yl}phenol；4-[1-[4-(2-hydroxyethoxy)phenyl]-2-phenylbut-1-enyl]phenol
• CAS: 110025-27-9
• 化学式: C₂₄H₂₄O₃
• 分子量: 360.453
• InChiKey: JDMRZCIEPITQKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-双(4-羟基苯基)-2-苯基丁-1-烯 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.17h， 生成 4-(1-(4-(2-hydroxyethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
  参考文献：
  名称：

  Design and Synthesis of Norendoxifen Analogues with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities

  摘要：

  Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of breast cancer. Our previous efforts led to the discovery of norendoxifen as the first compound with dual aromatase inhibitory and estrogen receptor binding activities. To optimize its efficacy and aromatase selectivity versus other cytochrome P450 enzyme, a series of structurally related norendoxifen analogues were designed and synthesized. The most potent compound, 4'-hydroxynorendoxifen (10), displayed elevated inhibitory potency against aromatase and enhanced affinity for estrogen receptors when compared to norendoxifen. The selectivity of 10 for aromatase versus other cytochrome P450 eniymes was also superior to norendoxifen. 4'-Hydroxynorendoxifen is therefore an interesting lead for further development to obtain new anticancer agents of potential value for the treatment of breast cancer.

  DOI：

  10.1021/jm501218e

文献信息

• Design and Synthesis of Norendoxifen Analogues with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities
  作者：Wei Lv、Jinzhong Liu、Todd C. Skaar、David A. Flockhart、Mark Cushman

  DOI：10.1021/jm501218e

  日期：2015.3.26

  Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of breast cancer. Our previous efforts led to the discovery of norendoxifen as the first compound with dual aromatase inhibitory and estrogen receptor binding activities. To optimize its efficacy and aromatase selectivity versus other cytochrome P450 enzyme, a series of structurally related norendoxifen analogues were designed and synthesized. The most potent compound, 4'-hydroxynorendoxifen (10), displayed elevated inhibitory potency against aromatase and enhanced affinity for estrogen receptors when compared to norendoxifen. The selectivity of 10 for aromatase versus other cytochrome P450 eniymes was also superior to norendoxifen. 4'-Hydroxynorendoxifen is therefore an interesting lead for further development to obtain new anticancer agents of potential value for the treatment of breast cancer.