2-[2-(3,4-dichlorophenyl)ethylamino]-1-pyridin-3-ylethanol | 875811-94-2

• 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-[2-(3,4-dichlorophenyl)ethylamino]-1-pyridin-3-ylethanol
• CAS: 875811-94-2
• 化学式: C₁₅H₁₆Cl₂N₂O
• 分子量: 311.211
• InChiKey: MNAMBPLSSOVBOO-UHFFFAOYSA-N

物化性质

• 沸点：
  479.6±40.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(3,4-dichlorophenyl)ethylamino]-1-pyridin-3-ylethanol 、 丙醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 LK-935
  参考文献：
  名称：

  Synthesis, Conformation, and Stereodynamics of a Salt of 2-{[2-(3,4-Dichlorophenyl)- ethyl]propylamino}-1-pyridin-3-ylethanol

  摘要：

  [GRAPHIC]A novel synthetic route was developed for 2-{[2-(3,4-dichlorophenyl)ethyl]propylamino}-1-pyridin-3-yiethanol (4). A dynamic process due to nitrogen inversion at the central amine nitrogen has been identified by NMR spectroscopy for the dihydrobromide salt of this compound. The conformational properties of the diastereomeric pair were determined by analysis of NOE connectivities and MO calculations.

  DOI：

  10.1021/jo051455f
• 作为产物：
  描述：

  3-(2-溴乙酰基)吡啶氢溴酸盐 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-[2-(3,4-dichlorophenyl)ethylamino]-1-pyridin-3-ylethanol
  参考文献：
  名称：

  Synthesis, Conformation, and Stereodynamics of a Salt of 2-{[2-(3,4-Dichlorophenyl)- ethyl]propylamino}-1-pyridin-3-ylethanol

  摘要：

  [GRAPHIC]A novel synthetic route was developed for 2-{[2-(3,4-dichlorophenyl)ethyl]propylamino}-1-pyridin-3-yiethanol (4). A dynamic process due to nitrogen inversion at the central amine nitrogen has been identified by NMR spectroscopy for the dihydrobromide salt of this compound. The conformational properties of the diastereomeric pair were determined by analysis of NOE connectivities and MO calculations.

  DOI：

  10.1021/jo051455f

文献信息

• Novel cholesterol biosynthesis inhibitors targeting human lanosterol 14α-demethylase (CYP51)
  作者：Tina Korošec、Jure Ačimovič、Matej Seliškar、Darko Kocjan、Klementina Fon Tacer、Damjana Rozman、Uroš Urleb

  DOI：10.1016/j.bmc.2007.10.001

  日期：2008.1

  Novel cholesterol biosynthesis inhibitors, a group of pyridylethanol(phenylethyl)amine derivatives, were synthesized. Sterol profiling assay in the human hepatoma HepG2 cells revealed that compounds target human lanosterol 14alpha-demethylase (CYP51). Structure-activity relationship study of the binding with the overexpressed human CYP51 indicates that the pyridine binds within the heme binding pocket

  合成了新型胆固醇生物合成抑制剂，一组吡啶基乙醇（苯乙基）胺衍生物。在人肝癌HepG2细胞中的甾醇谱分析表明该化合物靶向人羊毛甾醇14α-脱甲基酶（CYP51）。与过量表达的人CYP51结合的结构-活性关系研究表明，吡啶与唑类类似物在血红素结合口袋中结合。