5-Methyl-4-(3-nitro-benzoyl)-isoxazole-3-carboxylic acid ethyl ester | 189306-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-4-(3-nitro-benzoyl)-isoxazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-methyl-4-(3-nitrobenzoyl)-1,2-oxazole-3-carboxylate
• CAS: 189306-87-4
• 化学式: C₁₄H₁₂N₂O₆
• 分子量: 304.259
• InChiKey: CLUZATJHYCVBHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Methyl-4-(3-nitro-benzoyl)-isoxazole-3-carboxylic acid ethyl ester 在 ammonium cerium(IV) nitrate 、 硝酸 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 6-Ethyl-3-methyl-4-(3-nitro-phenyl)-7-oxo-6,7-dihydro-thieno[2,3-d]pyridazine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel Heterocyclic-Fused Pyridazinones as Potent and Selective Phosphodiesterase IV Inhibitors

  摘要：

  A series of 6-aryl-4,5-heterocyclic-fused pyridazinones were designed and synthesized as selective phosphodiesterase (PDE) TV inhibitors. Biological evaluation of these compounds demonstrated a good selectivity profile toward the PDE TV family and greatly attenuated affinity for the Rolipram high-affinity binding site that seems to be responsible for undesiderable side effects. Structure-activity relationships (SARs) studies showed that the presence of an ethyl group at pyridazine N-2 is associated with the best potency and selectivity profile.

  DOI：

  10.1021/jm970105l
• 作为产物：
  描述：

  1-(3-硝基苯基)-1,3-丁二酮 、 ethyl chloroacetohydroximate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以67%的产率得到5-Methyl-4-(3-nitro-benzoyl)-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel Heterocyclic-Fused Pyridazinones as Potent and Selective Phosphodiesterase IV Inhibitors

  摘要：

  A series of 6-aryl-4,5-heterocyclic-fused pyridazinones were designed and synthesized as selective phosphodiesterase (PDE) TV inhibitors. Biological evaluation of these compounds demonstrated a good selectivity profile toward the PDE TV family and greatly attenuated affinity for the Rolipram high-affinity binding site that seems to be responsible for undesiderable side effects. Structure-activity relationships (SARs) studies showed that the presence of an ethyl group at pyridazine N-2 is associated with the best potency and selectivity profile.

  DOI：

  10.1021/jm970105l

文献信息

• Novel Heterocyclic-Fused Pyridazinones as Potent and Selective Phosphodiesterase IV Inhibitors
  作者：Vittorio Dal Piaz、Maria Paola Giovannoni、Carla Castellana、José Maria Palacios、Jorge Beleta、Teresa Doménech、Victor Segarra

  DOI：10.1021/jm970105l

  日期：1997.5.1

  A series of 6-aryl-4,5-heterocyclic-fused pyridazinones were designed and synthesized as selective phosphodiesterase (PDE) TV inhibitors. Biological evaluation of these compounds demonstrated a good selectivity profile toward the PDE TV family and greatly attenuated affinity for the Rolipram high-affinity binding site that seems to be responsible for undesiderable side effects. Structure-activity relationships (SARs) studies showed that the presence of an ethyl group at pyridazine N-2 is associated with the best potency and selectivity profile.