3'-methoxy-E-diethylstilbestrol dibenzoate | 1369506-06-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 3'-methoxy-E-diethylstilbestrol dibenzoate
• 英文别名: [4-[(E)-4-(4-benzoyloxy-3-methoxyphenyl)hex-3-en-3-yl]phenyl] benzoate
• CAS: 1369506-06-8
• 化学式: C₃₃H₃₀O₅
• 分子量: 506.598
• InChiKey: OTPMQJTVKXYHAF-ZQHSETAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-methoxy-E-diethylstilbestrol dibenzoate 在 乙醇 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以62.7%的产率得到3'-methoxy-E-diethylstilbestrol
  参考文献：
  名称：

  Synthesis of 3′-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors

  摘要：

  3'-Methoxy-E-diethylstilbestrol (2), with the structural and original similarities to 2-methoxyestradiol (2-ME2, 1), was synthesized and screened against HUVEC and a series of human cancer cell lines including RL95-2, SKOV-3, MCF-7 and T-47D in vitro. The configuration of the title compound was determined via the single crystal X-ray diffraction of its benzoyl-ester derivative (10). The fact that 3'-methoxy-E-diethylstilbestrol and its analogues (8 and 11) showed potential antiangiogenesis and anti-tumor activities at a close level, whereas its ester derivative (10) did not display any cytotoxic activities on all the screening cell lines indicated that the core scaffold of 3'-methoxy-3,4-diphenylhexane and the exposed hydroxyl-groups in the structures are essential pharmacophores for their anti-tumor activities. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.12.024
• 作为产物：
  描述：

  1-(4-benzyloxy-3-methoxyphenyl)-2-(4-benzyloxyphenyl)butan-1-one 在 硫酸 、 5%-palladium/activated carbon 、 氢溴酸 、 甲酸铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 55.5h， 生成 3'-methoxy-E-diethylstilbestrol dibenzoate
  参考文献：
  名称：

  Synthesis of 3′-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors

  摘要：

  3'-Methoxy-E-diethylstilbestrol (2), with the structural and original similarities to 2-methoxyestradiol (2-ME2, 1), was synthesized and screened against HUVEC and a series of human cancer cell lines including RL95-2, SKOV-3, MCF-7 and T-47D in vitro. The configuration of the title compound was determined via the single crystal X-ray diffraction of its benzoyl-ester derivative (10). The fact that 3'-methoxy-E-diethylstilbestrol and its analogues (8 and 11) showed potential antiangiogenesis and anti-tumor activities at a close level, whereas its ester derivative (10) did not display any cytotoxic activities on all the screening cell lines indicated that the core scaffold of 3'-methoxy-3,4-diphenylhexane and the exposed hydroxyl-groups in the structures are essential pharmacophores for their anti-tumor activities. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.12.024

文献信息

• Synthesis of 3′-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors
  作者：Qian Liu、Weiwei Jin、Yan Zhu、Jieyun Zhou、Min Lu、Qian Zhang

  DOI：10.1016/j.steroids.2011.12.024

  日期：2012.4

  3'-Methoxy-E-diethylstilbestrol (2), with the structural and original similarities to 2-methoxyestradiol (2-ME2, 1), was synthesized and screened against HUVEC and a series of human cancer cell lines including RL95-2, SKOV-3, MCF-7 and T-47D in vitro. The configuration of the title compound was determined via the single crystal X-ray diffraction of its benzoyl-ester derivative (10). The fact that 3'-methoxy-E-diethylstilbestrol and its analogues (8 and 11) showed potential antiangiogenesis and anti-tumor activities at a close level, whereas its ester derivative (10) did not display any cytotoxic activities on all the screening cell lines indicated that the core scaffold of 3'-methoxy-3,4-diphenylhexane and the exposed hydroxyl-groups in the structures are essential pharmacophores for their anti-tumor activities. (C) 2011 Elsevier Inc. All rights reserved.