3-(4'-ethoxybenzyloxy)-4-methoxycinnamic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4'-ethoxybenzyloxy)-4-methoxycinnamic acid ethyl ester
• 英文别名: Ethyl 3-[3-[(4-ethoxyphenyl)methoxy]-4-methoxyphenyl]prop-2-enoate；ethyl 3-[3-[(4-ethoxyphenyl)methoxy]-4-methoxyphenyl]prop-2-enoate
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: PRTNWAJOFQKCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4'-ethoxybenzyloxy)-4-methoxycinnamic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以60.1%的产率得到3-(4'-ethoxybenzyloxy)-4-methoxycinnamic alcohol
  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 哌啶 、 potassium carbonate 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 9.0h， 生成 3-(4'-ethoxybenzyloxy)-4-methoxycinnamic 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

文献信息

• Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives
  作者：Hong-Bin Zou、Liang Zhang、Lei-Xiang Yang、Liu-Qing Yang、Yu Zhao、Yong-Ping Yu、Joachim Stöckigt

  DOI：10.1080/14786410902830175

  日期：2011.2

  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.