3-(4-allyloxyphenyl)acrylic acid methyl ester | 861621-06-9

• 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-(4-allyloxyphenyl)acrylic acid methyl ester
• 英文别名: Methyl 3-(4-prop-2-enoxyphenyl)prop-2-enoate；methyl 3-(4-prop-2-enoxyphenyl)prop-2-enoate
• CAS: 861621-06-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: XBTWYMHLGRRWAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-allyloxyphenyl)acrylic acid methyl ester 在 N,N-二乙基苯胺 作用下， 反应 5.0h， 以65%的产率得到3-(4-hydroxy-3-allylphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis

  摘要：

  The tumor microenvironment is characterized by hypoxia, low-nutrient levels, and acidosis. A natural product chemistry-based approach was used to discover small molecules that modulate adaptive responses to a hypoxic microenvironment through the hypoxia-inducible factor (HIF)-1 signaling pathways. Five compounds, such as baccharin (3), beturetol (4), kaempferide (5), isosakuranetin (6), and drupanin (9), that modulate HIF-1-dependent luciferase activity were identified from Brazilian green propolis using reporter assay. Compounds 3, 9 and 5 reduced HIF-1-dependent luciferase activity. The cinnamic acid derivatives 3 and 9 significantly inhibited expression of the HIF-1 alpha protein and HIF-1 downstream target genes such as glucose transporter 1, hexokinase 2, and vascular endothelial growth factor A. They also exhibited significant anti-angiogenic effects in the chick chorioallantoic membrane (CAM) assay at doses of 300 ng/CAM. On the other hand, flavonoids 4 and 6 induced HIF-1-dependent luciferase activity and expression of HIF-1 target genes under hypoxia. The contents (g/100 g extract) of the HIF-1-modulating compounds in whole propolis ethanol extracts were also determined based on liquid chromatography-electrospray ionization mass spectrometry as 1.6 (3), 14.2 (4), 4.0 (5), 0.7 (6), and 0.7 (9), respectively. These small molecules screened from Brazilian green propolis may be useful as lead compounds for the development of novel therapies against ischemic cardiovascular disease and cancer based on their ability to induce or inhibit HIF-1 activity, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.060
• 作为产物：
  描述：

  4-羟基肉桂酸甲酯 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以92%的产率得到3-(4-allyloxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis

  摘要：

  The tumor microenvironment is characterized by hypoxia, low-nutrient levels, and acidosis. A natural product chemistry-based approach was used to discover small molecules that modulate adaptive responses to a hypoxic microenvironment through the hypoxia-inducible factor (HIF)-1 signaling pathways. Five compounds, such as baccharin (3), beturetol (4), kaempferide (5), isosakuranetin (6), and drupanin (9), that modulate HIF-1-dependent luciferase activity were identified from Brazilian green propolis using reporter assay. Compounds 3, 9 and 5 reduced HIF-1-dependent luciferase activity. The cinnamic acid derivatives 3 and 9 significantly inhibited expression of the HIF-1 alpha protein and HIF-1 downstream target genes such as glucose transporter 1, hexokinase 2, and vascular endothelial growth factor A. They also exhibited significant anti-angiogenic effects in the chick chorioallantoic membrane (CAM) assay at doses of 300 ng/CAM. On the other hand, flavonoids 4 and 6 induced HIF-1-dependent luciferase activity and expression of HIF-1 target genes under hypoxia. The contents (g/100 g extract) of the HIF-1-modulating compounds in whole propolis ethanol extracts were also determined based on liquid chromatography-electrospray ionization mass spectrometry as 1.6 (3), 14.2 (4), 4.0 (5), 0.7 (6), and 0.7 (9), respectively. These small molecules screened from Brazilian green propolis may be useful as lead compounds for the development of novel therapies against ischemic cardiovascular disease and cancer based on their ability to induce or inhibit HIF-1 activity, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.060

文献信息

• Concise total synthesis of (±)-serotobenine
  作者：Kangjiang Liang、Ting Wu、Chengfeng Xia

  DOI：10.1039/c6ob00682e

  日期：——

  A concise total synthesis of (±)-serotobenine via a strategy inspired by the biosynthetic hypothesis for this alkaloid was accomplished. The indolofuran core was constructed by an iron-catalyzed intermolecular oxidative radical cross-coupling reaction developed by our group.

  通过该生物碱的生物合成假说启发的策略，完成了简明的（±）-serotobenine的全合成。吲哚呋喃核是通过我们小组开发的铁催化的分子间氧化自由基交叉偶联反应构建的。