1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-phenyl-piperazine | 23337-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-phenyl-piperazine
• 英文别名: 1-[(5‑methoxy‑2,3-dihydro-1-benzofuran-2-yl)methyl]-4-phenylpiperazine
• CAS: 23337-48-6
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: MJZPXFICAYYNLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯酚 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.5h， 生成 1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-phenyl-piperazine
  参考文献：
  名称：

  Novel potent vasodilating agents: Evaluation of the activity and potency of LINS01005 and derivatives in rat aorta

  摘要：

  Cardiovascular diseases (CVDs) present high prevalence rates in the current world. It is estimated that approximately one-third of the global deaths are related to CVD5, and thus there is still a need for novel drugs to treat these disorders. We serendipitously discovered that LINS01005 (5a) is a potent vasodilating agent in rat aorta, and therefore a set of analogues were evaluated for the vasodilating potency in Wistar and SHR rat thoracic aorta precontracted with norepinephrine, with endothelium intact (E+) or denuded (E-) aortic rings. Compounds 5a and 5b were the most potent, showing submicromolar potency for endothelium intact vessels (EC50 853 and 941 nM, respectively) and micromolar values for E- vessels (EC50 2.4 and 7.1 pM, respectively). These compounds were indeed significantly more potent vasodilating agents in SHR-derived aortic rings (p < 0.001), showing nanomolar potency for 5a [EC50 2.4 nM (E+) 9.0 nM (E-)] and 5b [EC50 20 nM (E+) 2.1 mu M (E-)]. SAR analysis though PCA and HCA were performed, suggesting that N-phenylpiperazine is essential to the activity, while increasing volume in the substituted aromatic moiety is detrimental to the potency. This is the first report of the vasodilating properties of such compounds, and studies regarding the mechanism of action are in progress in our group.

  DOI：

  10.1016/j.ejps.2019.105171