(Z)-1,2-difluoro-1-(3,4,5-trimethoxyphenyl)-2-(4-methoxy-3-tert-butyl-dimethyl-silyloxyphenyl)ethene | 824976-10-5

• 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: (Z)-1,2-difluoro-1-(3,4,5-trimethoxyphenyl)-2-(4-methoxy-3-tert-butyl-dimethyl-silyloxyphenyl)ethene
• 英文别名: tert-butyl-[5-[(Z)-1,2-difluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenoxy]-dimethylsilane
• CAS: 824976-10-5
• 化学式: C₂₄H₃₂F₂O₅Si
• 分子量: 466.597
• InChiKey: TVPTYYGVLWOQHK-DQRAZIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-1,2-difluoro-1-(3,4,5-trimethoxyphenyl)-2-(4-methoxy-3-tert-butyl-dimethyl-silyloxyphenyl)ethene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(Z)-1,2-difluoro-1-(3,4,5-trimethoxyphenyl)-2-(3-hydroxy-4-methoxyphenyl) ethene
  参考文献：
  名称：

  [EN] FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF
  [FR] FLUOROCOMBRETASTATINE ET SES DERIVES

  摘要：

  公开号：

  WO2005007603A3
• 作为产物：
  描述：

  (E)-1-bromo-1,2-difluoro-2-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl)ethene 、 3,4,5-三甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 以81%的产率得到(Z)-1,2-difluoro-1-(3,4,5-trimethoxyphenyl)-2-(4-methoxy-3-tert-butyl-dimethyl-silyloxyphenyl)ethene
  参考文献：
  名称：

  [EN] FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF
  [FR] FLUOROCOMBRETASTATINE ET SES DERIVES

  摘要：

  公开号：

  WO2005007603A3

文献信息

• [EN] FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF<br/>[FR] FLUOROCOMBRETASTATINE ET SES DERIVES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2005007603A3

  公开（公告）日：2005-07-07
• Synthesis and Biological Activity of Fluorinated Combretastatin Analogues
  作者：Domenico Alloatti、Giuseppe Giannini、Walter Cabri、Isabella Lustrati、Mauro Marzi、Andrea Ciacci、Grazia Gallo、M. Ornella Tinti、Marcella Marcellini、Teresa Riccioni、Mario B. Guglielmi、Paolo Carminati、Claudio Pisano

  DOI：10.1021/jm701362m

  日期：2008.5.1

  With the aim of understanding the influence of fluorine on the double bond of the cis-stilbene moiety of combretastatin derivatives and encouraged by a preliminary molecular modeling study showing a different biological environment on the interaction site with tubulin, we prepared, through various synthetic approaches, a small library of compounds in which one or both of the olefinic hydrogens were replaced with fluorine. X-ray analysis on the difluoro-CA-4 analogue demonstrated that the spatial arrangement of the molecule was not modified, compared to its nonfluorinated counterpart. SAR analysis confirmed the importance of the cis-stereochemistry of the stilbene scaffold. Nevertheless, some unpredicted results were observed on a few trans-fluorinated derivatives. The position of a fluorine atom on the double bond may affect the inhibition of tubulin polymerization and cytotoxic activity of these compounds.