N-[3-Hydroxy-5-(4-methoxy-phenyl)-1H-pyrazol-4-yl]-benzamide | 122019-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[3-Hydroxy-5-(4-methoxy-phenyl)-1H-pyrazol-4-yl]-benzamide
• CAS: 122019-69-6
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: DMUGWOKAOMQENQ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-[3-Hydroxy-5-(4-methoxy-phenyl)-1H-pyrazol-4-yl]-benzamide 在 盐酸 作用下， 以55%的产率得到4-Amino-5-(4-methoxy-phenyl)-1H-pyrazol-3-ol; hydrochloride
  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-Benzoylamino-3-(4-methoxy-phenyl)-3-oxo-propionic acid ethyl ester; hydrochloride 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N-[3-Hydroxy-5-(4-methoxy-phenyl)-1H-pyrazol-4-yl]-benzamide
  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