E-1-(p-aminophenyl)-1,2-di(p-t-butyldimethylsiloxyphenyl)-but-1-ene | 1431942-12-9

• 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: E-1-(p-aminophenyl)-1,2-di(p-t-butyldimethylsiloxyphenyl)-but-1-ene
• CAS: 1431942-12-9
• 化学式: C₃₄H₄₉NO₂Si₂
• 分子量: 559.94
• InChiKey: PBSGBEKJLXEUFS-QNEJGDQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.41
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (η5-C5H4COCl)Mn(CO)3 、 E-1-(p-aminophenyl)-1,2-di(p-t-butyldimethylsiloxyphenyl)-but-1-ene 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以123 mg的产率得到E-1-(p-tricarbonylcyclopentadienylmanganese carboxy-amino-phenyl)-1,2-di(p-tert-butyldimethylsiloxyphenyl)-but-1-ene
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of ferrocenyl and cymantrenyl triaryl butene on breast cancer cells. Biodistribution study of the corresponding technetium-99m tamoxifen conjugate

  摘要：

  1-(p-(ferrocenylcarbonylamino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 1, and 1-(p-(cymantrenylcarbonylamino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 2, were synthesized. Both compounds exhibit a significant antiproliferative effect against hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cells (IC50 = 4.5 and 9.4 mu M for 1 and 2 respectively on MDA-MB-231 and around 1 mu M for 1 and 2 on MCF-7 cells). Interestingly, 2 is the first cymantrenyl complex in this triaryl butene series to show such a high cytotoxic effect. A metal exchange reaction between I and (TcO4-)-Tc-99m was used for the synthesis of 1-(p-(tricarbonylcyclopentadienyl-[Tc-99m]-technetium carboxy-amino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 3. Tc-99m-3 was obtained in 70-75% yield. The in vivo biodistribution of purified Tc-99m-3 was undertaken on mature female Wistar rats. The uptake by organs follows the order: liver > lung > kidney > heart > spleen > ovaries > bone > muscle > uterus. The ovaries/muscle ratio was 3.89 while that of uterus/muscle ratio was 0.99. Uptake in ovaries was abolished by co-administration of 17 beta-estradiol while that of most organs devoided of estrogen receptors remained unchanged. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.11.035
• 作为产物：
  描述：

  4-amino-4'-t-butyldimethylsilyl-benzophenone 、 4-t-butyldimethylsilyl-propiophenone 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以26%的产率得到Z-1-(p-aminophenyl)-1,2-di(p-t-butyldimethylsiloxyphenyl)-but-1-ene
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of ferrocenyl and cymantrenyl triaryl butene on breast cancer cells. Biodistribution study of the corresponding technetium-99m tamoxifen conjugate

  摘要：

  1-(p-(ferrocenylcarbonylamino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 1, and 1-(p-(cymantrenylcarbonylamino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 2, were synthesized. Both compounds exhibit a significant antiproliferative effect against hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cells (IC50 = 4.5 and 9.4 mu M for 1 and 2 respectively on MDA-MB-231 and around 1 mu M for 1 and 2 on MCF-7 cells). Interestingly, 2 is the first cymantrenyl complex in this triaryl butene series to show such a high cytotoxic effect. A metal exchange reaction between I and (TcO4-)-Tc-99m was used for the synthesis of 1-(p-(tricarbonylcyclopentadienyl-[Tc-99m]-technetium carboxy-amino-phenyl)-1,2-di(p-hydroxyphenyl)-but-1-ene, 3. Tc-99m-3 was obtained in 70-75% yield. The in vivo biodistribution of purified Tc-99m-3 was undertaken on mature female Wistar rats. The uptake by organs follows the order: liver > lung > kidney > heart > spleen > ovaries > bone > muscle > uterus. The ovaries/muscle ratio was 3.89 while that of uterus/muscle ratio was 0.99. Uptake in ovaries was abolished by co-administration of 17 beta-estradiol while that of most organs devoided of estrogen receptors remained unchanged. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.11.035