(2Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2-penten-1-ol | 1023327-77-6

• 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)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2-penten-1-ol
• 英文别名: (Z)-5-[4-[(4-ethoxyphenyl)methoxy]-3,5-dimethoxyphenyl]pent-2-en-1-ol
• CAS: 1023327-77-6
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: RXOZNJDVPXQCAV-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-dimethoxy-4-(4-ethoxybenzyloxy)benzaldehyde 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 3.5h， 生成 (2Z,4Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2,4-pentadien-1-ol 、 (2Z)-5-[3',5'-dimethoxy-4'-(4''-ethoxybenzyloxy)phenyl]-2-penten-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

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.