ethyl 6-ethyl-3-methyl-7-oxo-4-phenyl-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate | 189307-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 6-ethyl-3-methyl-7-oxo-4-phenyl-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate
• CAS: 189307-06-0
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: WQNMIKTWUSWXJP-UHFFFAOYSA-N

物化性质

• 沸点：
  524.8±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-ethyl-3-methyl-7-oxo-4-phenyl-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到6-Ethyl-3-methyl-7-oxo-4-phenyl-6,7-dihydro-1H-pyrrolo[2,3-d]pyridazine-2-carboxylic acid
  参考文献：
  名称：

  Heterocyclic-fused 3(2H)-pyridazinones as potent and selective PDE IV inhibitors: Further structure-activity relationships and molecular modelling studies

  摘要：

  DOI：

  10.1016/s0223-5234(99)80030-0
• 作为产物：
  描述：

  5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.83h， 生成 ethyl 6-ethyl-3-methyl-7-oxo-4-phenyl-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate
  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.
• Heterocyclic-fused 3(2H)-pyridazinones as potent and selective PDE IV inhibitors: Further structure-activity relationships and molecular modelling studies
  作者：Vittorio Dal Piaz、Maria Paola Giovannoni、Carla Castellana、José Maria Palacios、Jorge Beleta、Teresa Doménech、Victor Segarra

  DOI：10.1016/s0223-5234(99)80030-0

  日期：1998.10