1-methylpropyl 1-(3',4'-dihydroxyphenyl)propenoate

• 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: 1-methylpropyl 1-(3',4'-dihydroxyphenyl)propenoate
• 英文别名: sec-butyl caffeate；Butan-2-yl-3-(3,4-dihydroxyphenyl)prop-2-enoate；butan-2-yl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: FYIXPNKHXLKURD-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  二丁烷-2-基丙二酸酯 在 哌啶 、 吡啶 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-methylpropyl 1-(3',4'-dihydroxyphenyl)propenoate
  参考文献：
  名称：

  Xia, Chun-Nian; Hu, Wei-Xiao, Journal of Chemical Research, 2005, # 5, p. 332 - 334

  摘要：

  DOI：

文献信息

• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.
• Hu, Wei-Xiao; Xia, Chun-Nian; Wang, Guo-Hong, Journal of Chemical Research, 2006, # 9, p. 586 - 588
  作者：Hu, Wei-Xiao、Xia, Chun-Nian、Wang, Guo-Hong、Zhou, Wei

  DOI：——

  日期：——
• Synthesis and antitumor activity of feruloyl and caffeoyl derivatives
  作者：Hui-zhen Chen、You-bao Chen、Ya-ping Lv、Fang Zeng、Juan Zhang、Yong-lie Zhou、Han-bing Li、Li-fei Chen、Bin-jie Zhou、Jian-rong Gao、Chun-nian Xia

  DOI：10.1016/j.bmcl.2014.08.024

  日期：2014.9

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.
• Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
  作者：Koji Uwai、Yuu Osanai、Takuma Imaizumi、Syu-ichi Kanno、Mitsuhiro Takeshita、Masaaki Ishikawa

  DOI：10.1016/j.bmc.2008.07.006

  日期：2008.8

  Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of their activities remain unclear. Thus, in this study, we examined the function of the ester functional group and the alkyl side chain (alcoholic part) and transformed caffeic acid to several derivatives. The inhibitory effect of these derivatives on NO production in murine macrophage RAW264.7 cells was dependent on the length and size of the alkyl moiety, and undecyl caffeate was the most potent inhibitor of NO production. In addition, individual experiments using undecanol, caffeic acid, undecanol plus caffeic acid, and undecyl caffeate showed that the connection between caffeic acid and the alkyl chain is critical for activity. Amide and ketone derivatives showed that not only the ester functional group but also the amide and ketone functional groups exhibit an inhibitory effect on NO production. (c) 2008 Elsevier Ltd. All rights reserved.
• Xia, Chun-Nian; Hu, Wei-Xiao, Journal of Chemical Research, 2005, # 5, p. 332 - 334
  作者：Xia, Chun-Nian、Hu, Wei-Xiao

  DOI：——

  日期：——