methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]acrylate

• 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: methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]acrylate
• 英文别名: palicatin B methyl ether；methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoate
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: PPFGVSIVQVZNNN-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]acrylate 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到Drupaninmonomethylether
  参考文献：
  名称：

  Structure−Antifungal Activity Relationship of Cinnamic Acid Derivatives

  摘要：

  A structure-antifungal activity relationship (SAR) study of 22 related cinnamic acid derivatives was carried out. Attention was focused on the antifungal activities exhibited against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. (E)-3-(4-Methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid (16) exhibited antifungal activity against A. niger, comparable to that of miconazole and a significant antifungal effect against A. flavus and A. terreus as well. A structure-activity relationship (SAR) study of related cinnamic acid derivatives has allowed a model to be proposed for the recognition of the minimal structural requirements for the antifungal effect in this series.

  DOI：

  10.1021/jf0729098
• 作为产物：
  描述：

  4-香豆酸 在 硫酸 、 sodium hydride 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 79.5h， 生成 methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]acrylate
  参考文献：
  名称：

  Structure−Antimutagenic Activity Relationship Study of Plicatin B

  摘要：

  A systematic structure-activity relationship study of plicatin B (1), an antimutagenic constituent of Psoralea juncea, was undertaken with a view toward elucidating its chemical mode of action and possibly optimizing its antimutagenic activity during the process. Compound 1 and its related analogues were examined for their antimutagenic activity against mutations induced by ethyl methanesulfonate, a direct acting mutagen and alkylating agent, in Salmonella typhimurium strain TA100, utilizing the modified Ames test protocol. The dihydro analogue 3 resulting from saturation of the conjugated alkene double bond of 1 was found to exhibit reduced cytotoxicity and enhanced efficacy relative to the parent compound. This result serves preliminarily to exclude a Michael acceptor role of the alpha,beta-unsaturated carbonyl moiety in connection with its antimutagenic activity.

  DOI：

  10.1021/np980304n

文献信息

• Structure−Antifungal Activity Relationship of Cinnamic Acid Derivatives
  作者：Fabricio Bisogno、Laura Mascoti、Cecilia Sanchez、Francisco Garibotto、Fernando Giannini、Marcela Kurina-Sanz、Ricardo Enriz

  DOI：10.1021/jf0729098

  日期：2007.12.1

  A structure-antifungal activity relationship (SAR) study of 22 related cinnamic acid derivatives was carried out. Attention was focused on the antifungal activities exhibited against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. (E)-3-(4-Methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid (16) exhibited antifungal activity against A. niger, comparable to that of miconazole and a significant antifungal effect against A. flavus and A. terreus as well. A structure-activity relationship (SAR) study of related cinnamic acid derivatives has allowed a model to be proposed for the recognition of the minimal structural requirements for the antifungal effect in this series.
• Structure−Antimutagenic Activity Relationship Study of Plicatin B
  作者：Sanjay R. Menon、Vishal K. Patel、Lester A. Mitscher、Peter Shih、Segaran P. Pillai、Delbert M. Shankel

  DOI：10.1021/np980304n

  日期：1999.1.1

  A systematic structure-activity relationship study of plicatin B (1), an antimutagenic constituent of Psoralea juncea, was undertaken with a view toward elucidating its chemical mode of action and possibly optimizing its antimutagenic activity during the process. Compound 1 and its related analogues were examined for their antimutagenic activity against mutations induced by ethyl methanesulfonate, a direct acting mutagen and alkylating agent, in Salmonella typhimurium strain TA100, utilizing the modified Ames test protocol. The dihydro analogue 3 resulting from saturation of the conjugated alkene double bond of 1 was found to exhibit reduced cytotoxicity and enhanced efficacy relative to the parent compound. This result serves preliminarily to exclude a Michael acceptor role of the alpha,beta-unsaturated carbonyl moiety in connection with its antimutagenic activity.