3,5-dimethoxy-4-(4'-ethoxybenzyloxy)cinnamic acid ethyl ester | 881855-03-4

• 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: 3,5-dimethoxy-4-(4'-ethoxybenzyloxy)cinnamic acid ethyl ester
• 英文别名: 4-O-(4-ethoxybenzyl)sinapic acid ethyl ester
• CAS: 881855-03-4
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: CMARYDJORHTORU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  3,5-dimethoxy-4-(4'-ethoxybenzyloxy)cinnamic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以96%的产率得到4-O-(4-ethoxybenzyl)sinapic acid
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056
• 作为产物：
  描述：

  3,4,5-三甲氧基苄醇 在 六甲基磷酰三胺 、 sodium hydride 、 potassium carbonate 、 苯硫酚 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 、 苯 为溶剂， 生成 3,5-dimethoxy-4-(4'-ethoxybenzyloxy)cinnamic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056

文献信息

• Synthesis, biological evaluation, and structure–activity relationship study of novel cytotoxic aza-caffeic acid derivatives
  作者：Hongbin Zou、Hao Wu、Xiangnan Zhang、Yu Zhao、Joachim Stöckigt、Yijia Lou、Yongping Yu

  DOI：10.1016/j.bmc.2010.07.016

  日期：2010.9

  Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl) prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 mu M, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.