N-(3-甲基-5-氧代-1,2-二氢吡唑-4-基)苯甲酰胺 | 122019-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-甲基-5-氧代-1,2-二氢吡唑-4-基)苯甲酰胺
• 英文名称: 4-benzoylamino-3-methyl-1H-pyrazol-5(2H)-one
• 英文别名: N-(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)benzamide
• CAS: 122019-46-9
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: GBFBJYWABPDRPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-甲基-5-氧代-1,2-二氢吡唑-4-基)苯甲酰胺 在 盐酸 作用下， 以27%的产率得到4-amino-3-methyl-1H-pyrazol-5-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-oxo-butyric acid methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到N-(3-甲基-5-氧代-1,2-二氢吡唑-4-基)苯甲酰胺
  参考文献：
  名称：

  将4-（1-二甲基氨基亚乙基）-2-苯基-5（4 H）-恶唑酮转化为2-苯甲酰基氨基-3-氧代丁酸甲酯。1-取代的4-苯甲酰基氨基-3-甲基-5（2 H）-吡唑啉酮的合成

  摘要：

  由马尿酸（1）制备2-苯甲酰基氨基-3-氧代丁酸甲酯（3），将其与N，N-二甲基乙酰胺和氯氧化磷转化为4-（1-二甲基氨基亚乙基）-2-苯基-5（4 H）-恶唑酮（2），然后用盐酸的甲醇溶液水解。用肼4处理化合物3，得到4-苯甲酰基氨基-3-甲基-1 H-吡唑-5（2 H）-one（6a）及其1-取代的衍生物6b-j。分离出相应的5f，i，j作为中间体。

  DOI：

  10.1002/jhet.5570350607

文献信息

• Homami, Seyed-Saied; Mukerjee, Arya K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 7, p. 411 - 414
  作者：Homami, Seyed-Saied、Mukerjee, Arya K

  DOI：——

  日期：——
• Evaluation and synthesis of amino-hydroxy isoxazoles and pyrazoles as potential glycine agonists
  作者：J. Drummond、G. Johnson、D. G. Nickell、D. F. Ortwine、R. F. Bruns、B. Welbaum

  DOI：10.1021/jm00129a016

  日期：1989.9

  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.
• Transformation of 4-(1-dimethylaminoethylidene)-2-phenyl-5(4<i>H</i>)-oxazolone into methyl 2-benzoylamino-3-oxobutanoate. The synthesis of 1-substituted 4-benzoylamino-3-methyl-5(2<i>H</i>)-pyrazolones
  作者：UrŠKa Bratušek、AleŠ Hvala、Branko Stanovnik

  DOI：10.1002/jhet.5570350607

  日期：1998.11

  Methyl 2-benzoylamino-3-oxobutanoate (3) was prepared from hippuric acid (1) which was converted with N,N-dimethylacetamide and phosphorus oxychloride into 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone (2) followed by hydrolysis with hydrochloric acid in methanol. Compound 3 was treated with hydrazines 4 to give 4-benzoylamino-3-methyl-1H-pyrazol-5(2H)-one (6a) and its 1-substituted derivatives

  由马尿酸（1）制备2-苯甲酰基氨基-3-氧代丁酸甲酯（3），将其与N，N-二甲基乙酰胺和氯氧化磷转化为4-（1-二甲基氨基亚乙基）-2-苯基-5（4 H）-恶唑酮（2），然后用盐酸的甲醇溶液水解。用肼4处理化合物3，得到4-苯甲酰基氨基-3-甲基-1 H-吡唑-5（2 H）-one（6a）及其1-取代的衍生物6b-j。分离出相应的5f，i，j作为中间体。