(E)-8-phenyl-7-octenyl caffeate

• 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: (E)-8-phenyl-7-octenyl caffeate
• 英文别名: [(E)-8-phenyloct-7-enyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: OZNOABNEAZHZDA-KMNNAZTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 (E)-8-phenyl-7-octenyl caffeate
  参考文献：
  名称：

  Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

  摘要：

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00138-4

文献信息

• Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
  作者：T Nagaoka

  DOI：10.1016/s0968-0896(02)00138-4

  日期：2002.10

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.