2-hydroxy-4-methoxy-5-(isopentenyl)benzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-4-methoxy-5-(isopentenyl)benzoic acid
• 英文别名: 2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)benzoic acid
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XBKQNBMJPBHXPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methoxy-5-(isopentenyl)benzoic acid 在 氨 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 以46.49%的产率得到2-hydroxy-4-methoxy-5-(isopentenyl)benzamide
  参考文献：
  名称：

  Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR alpha/beta agonist activity and equal PPAR-gamma agonist activity than does bavachinin.

  DOI：

  10.1007/s00044-018-2197-6
• 作为产物：
  描述：

  4-甲氧基水杨酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 硫酸 、 溴 、 caesium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.5h， 生成 2-hydroxy-4-methoxy-5-(isopentenyl)benzoic acid
  参考文献：
  名称：

  Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR alpha/beta agonist activity and equal PPAR-gamma agonist activity than does bavachinin.

  DOI：

  10.1007/s00044-018-2197-6

文献信息

• Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors
  作者：Jingyu Yi、Guoxin Du、Yuanyuan Zhao、Liuqiang Zhang、Bo Li、Weiliang Zhu、Cheng Huang、Yiming Li、Fujiang Guo

  DOI：10.1007/s00044-018-2197-6

  日期：2018.7

  Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR alpha/beta agonist activity and equal PPAR-gamma agonist activity than does bavachinin.