6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one | 1350848-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one
• 英文别名: 3-(2,6-dimethylanilino)-1H-pyridazin-6-one
• CAS: 1350848-81-5
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: ADBIZAROKSPVPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one 在 铁粉 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Discovery of novel 2,6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors

  摘要：

  2,6-Disubstituted pyridazinone 4 was identified by HTS as a novel acetylcholinesterase (AChE) inhibitor. Under SAR development, compound 17e stood out as displaying high AChE inhibitory activity and AChE/butyrylcholinesterase (BuChE) selectivity in vitro. Docking studies revealed that 17e might interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) simultaneously. Based on this novel binding information, 6-ortho-tolylamino and N-ethyl-N-isopropylacetamide substituted piperidine were disclosed as new PAS and CAS binders. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.056
• 作为产物：
  描述：

  2,6-二甲基苯胺 在 potassium carbonate 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 9.0h， 生成 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one
  参考文献：
  名称：

  Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives

  摘要：

  A series of pyridazinone-containing compounds were designed and synthesized as congeners for diclofenac, the most potent and widely used NSAID. The target compounds were evaluated for their anti-inflammatory activity on rat paw edema inflammation model against diclofenac as a reference compound. Seven of the tested compounds demonstrated more than 50% inhibition of carrageenan-induced rat paw edema at a dose 10 mg/kg. The compounds, 6-(2-bromophenylamino)pyridazin-3(2H)-one 2a and 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one 2e, displayed 74 and 73.5% inflammation-inhibitory activity, respectively, which is comparable to diclofenac (78.3%) at the same dose level after 4 h. The most active compounds as anti-inflammatory agents, 2a, 2e, and 6a, displayed fewer number of ulcers and milder ulcer score than indomethacin in ulcerogenicity screening.

  DOI：

  10.1007/s00044-011-9895-7

文献信息

• Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives
  作者：K. A. M. Abouzid、N. A. Khalil、E. M. Ahmed、A. Esmat、A. M. Al-Abd

  DOI：10.1007/s00044-011-9895-7

  日期：2012.11

  A series of pyridazinone-containing compounds were designed and synthesized as congeners for diclofenac, the most potent and widely used NSAID. The target compounds were evaluated for their anti-inflammatory activity on rat paw edema inflammation model against diclofenac as a reference compound. Seven of the tested compounds demonstrated more than 50% inhibition of carrageenan-induced rat paw edema at a dose 10 mg/kg. The compounds, 6-(2-bromophenylamino)pyridazin-3(2H)-one 2a and 6-(2,6-dimethylphenylamino)pyridazin-3(2H)-one 2e, displayed 74 and 73.5% inflammation-inhibitory activity, respectively, which is comparable to diclofenac (78.3%) at the same dose level after 4 h. The most active compounds as anti-inflammatory agents, 2a, 2e, and 6a, displayed fewer number of ulcers and milder ulcer score than indomethacin in ulcerogenicity screening.
• Discovery of novel 2,6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors
  作者：Weiqiang Xing、Yan Fu、Zhangxing Shi、Dong Lu、Haiyan Zhang、Youhong Hu

  DOI：10.1016/j.ejmech.2013.01.056

  日期：2013.5

  2,6-Disubstituted pyridazinone 4 was identified by HTS as a novel acetylcholinesterase (AChE) inhibitor. Under SAR development, compound 17e stood out as displaying high AChE inhibitory activity and AChE/butyrylcholinesterase (BuChE) selectivity in vitro. Docking studies revealed that 17e might interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) simultaneously. Based on this novel binding information, 6-ortho-tolylamino and N-ethyl-N-isopropylacetamide substituted piperidine were disclosed as new PAS and CAS binders. (c) 2013 Elsevier Masson SAS. All rights reserved.