3-(biphenyl-4-yl)-4-[3-(chloromethyl)-2-methylphenyl]-5-ethyl-4H-1,2,4-triazole | 1446690-53-4

• 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: 3-(biphenyl-4-yl)-4-[3-(chloromethyl)-2-methylphenyl]-5-ethyl-4H-1,2,4-triazole
• 英文别名: 4-[3-(Chloromethyl)-2-methylphenyl]-3-ethyl-5-(4-phenylphenyl)-1,2,4-triazole；4-[3-(chloromethyl)-2-methylphenyl]-3-ethyl-5-(4-phenylphenyl)-1,2,4-triazole
• CAS: 1446690-53-4
• 化学式: C₂₄H₂₂ClN₃
• 分子量: 387.912
• InChiKey: NZWAVKSGEGZTQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-(biphenyl-4-yl)-4-[3-(chloromethyl)-2-methylphenyl]-5-ethyl-4H-1,2,4-triazole 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以43%的产率得到3-(biphenyl-4-yl)-5-ethyl-4-[3-(methoxymethyl)-2-methylphenyl]-4H-1,2,4-triazole
  参考文献：
  名称：

  Atropisomeric 4-Phenyl-4H-1,2,4-triazoles as Selective Glycine Transporter 1 Inhibitors

  摘要：

  We report on the optimization of 4H-1,2,4-triazole derivatives to increase their activity and selectivity as glycine transporter 1 (GlyT1) inhibitors. Structure-activity relationship exploration resulted in the identification of a 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methyl-benzonitrile (14u) compound with markedly higher selectivity for GlyT1. Physiochemical studies revealed that 14u exists as a stable pair of atropisomers under physiological conditions. We successfully separated the atropisomers to obtain active enantiomer (R)-14u, which displayed favorable pharmacokinetic properties, as well as positive results in the mice Y-maze test.

  DOI：

  10.1021/jm400383w
• 作为产物：
  描述：

  {3-[3-(biphenyl-4-yl)-5-ethyl-4H-1,2,4-triazol-4-yl]-2-methylphenyl}methanol 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以99%的产率得到3-(biphenyl-4-yl)-4-[3-(chloromethyl)-2-methylphenyl]-5-ethyl-4H-1,2,4-triazole
  参考文献：
  名称：

  Atropisomeric 4-Phenyl-4H-1,2,4-triazoles as Selective Glycine Transporter 1 Inhibitors

  摘要：

  We report on the optimization of 4H-1,2,4-triazole derivatives to increase their activity and selectivity as glycine transporter 1 (GlyT1) inhibitors. Structure-activity relationship exploration resulted in the identification of a 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methyl-benzonitrile (14u) compound with markedly higher selectivity for GlyT1. Physiochemical studies revealed that 14u exists as a stable pair of atropisomers under physiological conditions. We successfully separated the atropisomers to obtain active enantiomer (R)-14u, which displayed favorable pharmacokinetic properties, as well as positive results in the mice Y-maze test.

  DOI：

  10.1021/jm400383w