ethyl 4-acetyl-1-ethyl-1,6-dihydro-5-nitro-6-oxopyridazine-3-carboxylate | 1228805-34-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ethyl 4-acetyl-1-ethyl-1,6-dihydro-5-nitro-6-oxopyridazine-3-carboxylate
• CAS: 1228805-34-2
• 化学式: C₁₁H₁₃N₃O₆
• 分子量: 283.241
• InChiKey: AIUYOJDHQDWVDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  121.4
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-acetyl-1-ethyl-1,6-dihydro-5-nitro-6-oxopyridazine-3-carboxylate 在 肼 作用下， 以 乙醇 为溶剂， 以80%的产率得到ethyl 6-ethyl-6,7-dihydro-3-methyl-7-oxo-2H-pyrazolo[3,4-d]pyridazine-4-carboxylate
  参考文献：
  名称：

  Functionalized pyrazoles and pyrazolo[3,4-d]pyridazinones: Synthesis and evaluation of their phosphodiesterase 4 inhibitory activity

  摘要：

  A series of pyrazoles and pyrazolo[3,4-d]pyridazinones were synthesized and evaluated for their PDE4 inhibitory activity. All the pyrazoles were found devoid of activity, whereas some of the novel pyrazolo[3,4-d]pyridazinones showed good activity as PDE4 inhibitors. The most potent compounds in this series showed an IC50 in the nanomolar range. The ability to inhibit TNF-alpha release in human PBMCs was determined for two representative compounds, finding values in the sub-micromolar range. SARs studies demonstrated that the best arranged groups around the heterocyclic core are 2-chloro-, 2-methyl- and 3-nitrophenyl at position 2, an ethyl ester at position 4 and a small alkyl group at position 6. Molecular modeling studies performed on a representative compound allowed to define its binding mode to the PDE4B isoform. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.066
• 作为产物：
  描述：

  ethyl 6-ethyl-3-methyl-7-oxo-6,7-dihydroisoxazolo[3,4-d]pyridazine-4-carboxylate 在 硝酸 、 溶剂黄146 、 ammonium cerium (IV) nitrate 作用下， 以 水 、 溶剂黄146 为溶剂， 以53%的产率得到ethyl 4-acetyl-1-ethyl-1,6-dihydro-5-nitro-6-oxopyridazine-3-carboxylate
  参考文献：
  名称：

  Functionalized pyrazoles and pyrazolo[3,4-d]pyridazinones: Synthesis and evaluation of their phosphodiesterase 4 inhibitory activity

  摘要：

  A series of pyrazoles and pyrazolo[3,4-d]pyridazinones were synthesized and evaluated for their PDE4 inhibitory activity. All the pyrazoles were found devoid of activity, whereas some of the novel pyrazolo[3,4-d]pyridazinones showed good activity as PDE4 inhibitors. The most potent compounds in this series showed an IC50 in the nanomolar range. The ability to inhibit TNF-alpha release in human PBMCs was determined for two representative compounds, finding values in the sub-micromolar range. SARs studies demonstrated that the best arranged groups around the heterocyclic core are 2-chloro-, 2-methyl- and 3-nitrophenyl at position 2, an ethyl ester at position 4 and a small alkyl group at position 6. Molecular modeling studies performed on a representative compound allowed to define its binding mode to the PDE4B isoform. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.066