(E)-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxyphenyl]-2-(2-hydroxy-phenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one | 1202168-40-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxyphenyl]-2-(2-hydroxy-phenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one
• 英文别名: (E)-3-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]-2-(2-hydroxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1202168-40-8
• 化学式: C₃₁H₃₈O₇Si
• 分子量: 550.724
• InChiKey: VFTFYMVWXUWAJY-XQNSMLJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxyphenyl]-2-(2-hydroxy-phenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(E)-3-(3-hydroxy-4-methoxy-phenyl)-2-(2-hydroxyphenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one
  参考文献：
  名称：

  Combretastatin-like chalcones as inhibitors of microtubule polymerisation. Part 2: Structure-based discovery of alpha-aryl chalcones

  摘要：

  Tubulin is an important molecular target in cancer chemotherapy. Antimitotic agents able to bind to the protein are currently under study, commonly used in the clinic to treat a variety of cancers and/or exploited as probes to investigate the protein's structure and function. Here we report the binding modes for a series of colchicinoids, combretastatin A4 and chalcones established from docking studies carried out on the structure of tubulin in complex with colchicine. The proposed models, in agreement with published biochemical data, show that combretastatin A4 binds to the colchicine site of beta-tubulin and that chalcones assume an orientation similar to that of podophyllotoxin. The models can be used to design a new class of podophyllotoxin mimics, the alpha-aryl chalcones, capable of binding to the colchicine-binding site of beta-tubulin with higher affinity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.044
• 作为产物：
  描述：

  2-羟基苯硼酸 、 (Z)-2-bromo-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 水 、 二乙胺 、 三苯基膦 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 1.0h， 以84%的产率得到(E)-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxyphenyl]-2-(2-hydroxy-phenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one
  参考文献：
  名称：

  Combretastatin-like chalcones as inhibitors of microtubule polymerisation. Part 2: Structure-based discovery of alpha-aryl chalcones

  摘要：

  Tubulin is an important molecular target in cancer chemotherapy. Antimitotic agents able to bind to the protein are currently under study, commonly used in the clinic to treat a variety of cancers and/or exploited as probes to investigate the protein's structure and function. Here we report the binding modes for a series of colchicinoids, combretastatin A4 and chalcones established from docking studies carried out on the structure of tubulin in complex with colchicine. The proposed models, in agreement with published biochemical data, show that combretastatin A4 binds to the colchicine site of beta-tubulin and that chalcones assume an orientation similar to that of podophyllotoxin. The models can be used to design a new class of podophyllotoxin mimics, the alpha-aryl chalcones, capable of binding to the colchicine-binding site of beta-tubulin with higher affinity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.044