5-{2-[2-(3,4-dimethoxyphenyl)ethylamino]ethyl}-2-methoxyphenol | 54370-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-{2-[2-(3,4-dimethoxyphenyl)ethylamino]ethyl}-2-methoxyphenol
• CAS: 54370-03-5
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: DOKWFRBJOAFYAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  59.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-{2-[2-(3,4-dimethoxyphenyl)ethylamino]ethyl}-2-methoxyphenol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以36%的产率得到2-[2-(3,4-dimethoxyphenyl)ethyl]-7-methoxy-3,4-dihydro-1H-isoquinolin-6-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：

  3,4-二甲氧基苯乙胺 在 lithium aluminium tetrahydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 生成 5-{2-[2-(3,4-dimethoxyphenyl)ethylamino]ethyl}-2-methoxyphenol
  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

文献信息

• Studies on the erythrina alkaloids. VIII. Alkaloids of Erythriuna X bidwillii Lindl. (4). Synthesis of erybidine by photochemical reaction.
  作者：KAZUO ITO、HITOSHI TANAKA

  DOI：10.1248/cpb.22.2108

  日期：——

  Irradiation of methanolic solution of amide (VIII) by a 100 W high pressure mercury lamp in the presence of sodium hydroxide afforded a mixture of three phenolic irradiation products, whose structures were proved to be IX, X and XI respectively on the basis of chemical and spectral studies. Among these photocyclization products, X was reducted with sodium borohydride and boron trifluoride to provide the amine (XIII), which was converted with formalin and sodium borohydride to erybidine (I).

  在氢氧化钠存在下，用100 W高压汞灯照射酰胺(VIII)的甲醇溶液，得到三种酚类照射产物的混合物，根据化学和化学性质证明其结构分别为IX、X和XI。光谱研究。在这些光环化产物中，X用硼氢化钠和三氟化硼还原以提供胺(XIII)，其用福尔马林和硼氢化钠转化为厄比啶(I)。