(2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadienoic acid ethyl ester | 1023327-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadienoic acid ethyl ester
• CAS: 1023327-73-2
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: IPTDZMJRFIAKDY-XOHWUJONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadienoic acid ethyl ester 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以43.4%的产率得到(2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadien-1-ol
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives

  摘要：

  Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5 mu M, respectively. The structure-activity relationships of the derivatives are discussed.

  DOI：

  10.1080/14786410902830175
• 作为产物：
  描述：

  1-(溴甲基)-4-乙氧基苯 在 sodium ethanolate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 (2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadienoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives

  摘要：

  Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5 mu M, respectively. The structure-activity relationships of the derivatives are discussed.

  DOI：

  10.1080/14786410902830175