2,2-dibromo-2-fluoro-1-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl) ethanol | 824976-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2-dibromo-2-fluoro-1-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl) ethanol
• 英文别名: 2,2-Dibromo-1-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]-2-fluoroethanol
• CAS: 824976-06-9
• 化学式: C₁₅H₂₃Br₂FO₃Si
• 分子量: 458.238
• InChiKey: IWFMOXDPHCSHJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dibromo-2-fluoro-1-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl) ethanol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64.5%的产率得到1,1-dibromo-1,2-difluoro-2-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl)ethane
  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：

  氟三溴甲烷 、 3-叔-丁基二甲基硅氧基-4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 以68%的产率得到2,2-dibromo-2-fluoro-1-(4-methoxy-3-tert-butyl-dimethylsilyloxyphenyl) ethanol
  参考文献：
  名称：

  Synthesis and Biological Activity of Fluorinated Combretastatin Analogues

  摘要：

  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.

  DOI：

  10.1021/jm701362m

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.