3-(4-hydroxy-3-isopent-2-en-1-ylphenyl)acrylic acid

• 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-hydroxy-3-isopent-2-en-1-ylphenyl)acrylic acid
• 英文别名: 3-prenyl-4-hydroxycinnamic acid；3-isoprenyl-p-Coumaric acid；drupanin；3-prenyl-p-coumaric acid；4-hydroxy-3-prenylcinnamic acid；3-[4-Hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: HZKNHDLUFBYIQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-isopent-2-en-1-ylphenyl)acrylic acid 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-(4-methoxy-3-prenylphenyl)acrylic acid
  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

• 咖啡酸-赖氨酸及其衍生物、制备方法和用途
  申请人：西安科技大学

  公开号：CN106349099B

  公开（公告）日：2018-08-07

  本发明公开了咖啡酸‑赖氨酸及其衍生物、制备方法和用途，结构如式I所示，R1、R2为H、OH、O 、OCO 、3‑methylbut‑2‑enyl或异戊烯基；R3为H、CH3、Bn、O 、OCO 、BnCH2、i‑Pr、t‑Bu或金刚烷基。通过小鼠的口服葡萄糖耐量实验，显示咖啡酸‑赖氨酸及其衍生物能够显著降低血糖，证实了咖啡酸‑赖氨酸及其衍生物抗糖尿病的作用，可制备相关药物：