5-phenylpyridine-2-carbohydrazide | 1446690-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-phenylpyridine-2-carbohydrazide
• 英文别名: 5-Phenylpyridine-2-carbohydrazide
• CAS: 1446690-49-8
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: QWUMZWYCCLYWAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-(2-Fluorophenyl)propanimidothioate 、 5-phenylpyridine-2-carbohydrazide 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以3%的产率得到2-[5-ethyl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]-5-phenylpyridine
  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：

  5-苯基吡啶甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 5-phenylpyridine-2-carbohydrazide
  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

文献信息

• Atropisomeric 4-Phenyl-4<i>H</i>-1,2,4-triazoles as Selective Glycine Transporter 1 Inhibitors
  作者：Takashi Sugane、Takahiko Tobe、Wataru Hamaguchi、Itsuro Shimada、Kyoichi Maeno、Junji Miyata、Takeshi Suzuki、Tetsuya Kimizuka、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1021/jm400383w

  日期：2013.7.25

  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.