2-methoxy-4-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol | 1395084-72-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 2-methoxy-4-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol
• 英文别名: 2-Methoxy-4-[2-[2-(4-methoxyphenyl)ethylamino]ethyl]phenol
• CAS: 1395084-72-6
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: LCKBDXUNXDDRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-methoxy-4-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以45%的产率得到6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinolin-7-ol
  参考文献：
  名称：

  A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors

  摘要：

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

  DOI：

  10.1021/jm3006096
• 作为产物：
  描述：

  高香草酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 生成 2-methoxy-4-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol
  参考文献：
  名称：

  A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors

  摘要：

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

  DOI：

  10.1021/jm3006096