4,5,6,7-tetrahydro-3-hydroxyisoxazolo<4,5-b>pyridine-4-carboxylic acid 1,1-dimethylethyl ester | 122019-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5,6,7-tetrahydro-3-hydroxyisoxazolo<4,5-b>pyridine-4-carboxylic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl 3-oxo-6,7-dihydro-5H-[1,2]oxazolo[4,5-b]pyridine-4-carboxylate
• CAS: 122019-55-0
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: BORBMEJHNCLCBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-3-hydroxyisoxazolo<4,5-b>pyridine-4-carboxylic acid 1,1-dimethylethyl ester 、 三氟乙酸 反应 0.08h， 以65%的产率得到4,5,6,7-tetrahydroisoxazolo<4,5-b>pyridin-3-ol trifluoroacetate
  参考文献：
  名称：

  Evaluation and synthesis of amino-hydroxy isoxazoles and pyrazoles as potential glycine agonists

  摘要：

  Except for structurally similar small amino acids, such as alanine, beta-alanine, and serine, compounds acting as glycine-receptor agonists are an unknown class of pharmacological agents. To investigate the potential of small, substituted heterocycles to act as glycine agonists, we have evaluated the similarities between glycine and a series of hydroxy- and amino-substituted pyrazoles and isoxazoles through complementary molecular modeling techniques. Using a "scorecard approach" to determine the overall similarity of projected agonist structures to glycine, we prioritized synthesis and subsequently prepared several novel derivatives. The biological activity of these compounds was compared to that of glycine by using a [3H]strychnine-mediated glycine receptor binding assay. Despite the close similarity in the calculated parameters when compared to glycine, no significant receptor-binding activity was observed for the targeted analogues. These results illustrate the structurally exacting nature of the glycine receptor.

  DOI：

  10.1021/jm00129a016
• 作为产物：
  描述：

  2-<(hydroxyamino)carbonyl>-3-oxo-1-piperidinedicarboxylic acid 1,1-dimethylethyl ester 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 生成 4,5,6,7-tetrahydro-3-hydroxyisoxazolo<4,5-b>pyridine-4-carboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Evaluation and synthesis of amino-hydroxy isoxazoles and pyrazoles as potential glycine agonists

  摘要：

  Except for structurally similar small amino acids, such as alanine, beta-alanine, and serine, compounds acting as glycine-receptor agonists are an unknown class of pharmacological agents. To investigate the potential of small, substituted heterocycles to act as glycine agonists, we have evaluated the similarities between glycine and a series of hydroxy- and amino-substituted pyrazoles and isoxazoles through complementary molecular modeling techniques. Using a "scorecard approach" to determine the overall similarity of projected agonist structures to glycine, we prioritized synthesis and subsequently prepared several novel derivatives. The biological activity of these compounds was compared to that of glycine by using a [3H]strychnine-mediated glycine receptor binding assay. Despite the close similarity in the calculated parameters when compared to glycine, no significant receptor-binding activity was observed for the targeted analogues. These results illustrate the structurally exacting nature of the glycine receptor.

  DOI：

  10.1021/jm00129a016