cis-1-formyl-2-(3,4,5-trimethoxyphenyl)cyclopropane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: cis-1-formyl-2-(3,4,5-trimethoxyphenyl)cyclopropane
• 英文别名: (1S,2R)-2-(3,4,5-trimethoxyphenyl)cyclopropane-1-carbaldehyde
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: LFHKFEKKBDCGQK-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  碘仿 、 cis-1-formyl-2-(3,4,5-trimethoxyphenyl)cyclopropane 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 trans-1-(E-2-iodovinyl)-2-(3',4',5'-trimethoxyphenyl)cyclopropane 、 cis-1-(E-2-iodovinyl)-2-(3',4',5'-trimethoxyphenyl)cyclopropane
  参考文献：
  名称：

  Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge

  摘要：

  A series of novel combretastatin A4 analogues, in which the cis-olefinic bridge is replaced by a cyclopropyl-vinyl or a cyclopropyl-amide moiety, were synthesized and evaluated for inhibition of tubulin polymerization and antiproliferative activity. The derivative 9a with a (cis,E)-cyclopropyl-vinyl unit is the most promising compound. As expected, molecular docking of 9a has shown that only one of the cis-cyclopropyl enantiomers is a good ligand for tubulin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.062
• 作为产物：
  描述：

  cis-1-hydroxymethyl-2-(3,4,5-trimethoxyphenyl)cyclopropane 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到cis-1-formyl-2-(3,4,5-trimethoxyphenyl)cyclopropane
  参考文献：
  名称：

  Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge

  摘要：

  A series of novel combretastatin A4 analogues, in which the cis-olefinic bridge is replaced by a cyclopropyl-vinyl or a cyclopropyl-amide moiety, were synthesized and evaluated for inhibition of tubulin polymerization and antiproliferative activity. The derivative 9a with a (cis,E)-cyclopropyl-vinyl unit is the most promising compound. As expected, molecular docking of 9a has shown that only one of the cis-cyclopropyl enantiomers is a good ligand for tubulin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.062

文献信息

• Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge
  作者：Nancy Ty、Julia Kaffy、Alban Arrault、Sylviane Thoret、Renée Pontikis、Joelle Dubois、Luc Morin-Allory、Jean-Claude Florent

  DOI：10.1016/j.bmcl.2009.01.062

  日期：2009.3

  A series of novel combretastatin A4 analogues, in which the cis-olefinic bridge is replaced by a cyclopropyl-vinyl or a cyclopropyl-amide moiety, were synthesized and evaluated for inhibition of tubulin polymerization and antiproliferative activity. The derivative 9a with a (cis,E)-cyclopropyl-vinyl unit is the most promising compound. As expected, molecular docking of 9a has shown that only one of the cis-cyclopropyl enantiomers is a good ligand for tubulin. (C) 2009 Elsevier Ltd. All rights reserved.