4-amino-3-(2-methylphenylamino)pyridine | 1189641-56-2

• 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: 4-amino-3-(2-methylphenylamino)pyridine
• 英文别名: n3-(2-Methylphenyl)pyridine-3,4-diamine；3-N-(2-methylphenyl)pyridine-3,4-diamine
• CAS: 1189641-56-2
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: QNKUTBZOIUZDHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酰氯 、 4-amino-3-(2-methylphenylamino)pyridine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以48%的产率得到N-[3-(2-methylphenylamino)-4-pyridinyl]trifluoromethanesulfonamide
  参考文献：
  名称：

  Pyridine Analogues of Nimesulide: Design, Synthesis, and in Vitro and in Vivo Pharmacological Evaluation as Promising Cyclooxygenase 1 and 2 Inhibitors

  摘要：

  Nonsteroidal anti-inflammatory drugs (NSAIDs) represent one of the most prescribed medications, although the chronic use of such pharmacological agents is commonly associated with numerous side effects. The demonstration that the use of COX-2 selective or preferential inhibitors is associated with a better tolerability opened new horizons in the search of safer drugs for the management of inflammation. In the present study, we report the synthesis and the pharmacological evaluation of pyridine analogues of nimesulide, a COX-2 preferential inhibitor. The cyclooxygenases (COXs) inhibitory activities were evaluated in vitro using a human whole blood model. According to the in vitro results, a selection of compounds exhibiting moderate to high COX-2/COX-1 selectivity ratio (from weak COX-2 preferential inhibitors to compounds displaying a celecoxib-like selectivity profile) were further evaluated in vivo in a model of A carrageenan-induced pleurisy in rats. Some of the selected compounds displayed similar or improved anti-inflammatory properties when compared to nimesulide and celecoxib.

  DOI：

  10.1021/jm900702b
• 作为产物：
  描述：

  4-Nitro-3-(o-tolylamino)-pyridin-N-oxid 在 铁粉 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 4-amino-3-(2-methylphenylamino)pyridine
  参考文献：
  名称：

  Pyridine Analogues of Nimesulide: Design, Synthesis, and in Vitro and in Vivo Pharmacological Evaluation as Promising Cyclooxygenase 1 and 2 Inhibitors

  摘要：

  Nonsteroidal anti-inflammatory drugs (NSAIDs) represent one of the most prescribed medications, although the chronic use of such pharmacological agents is commonly associated with numerous side effects. The demonstration that the use of COX-2 selective or preferential inhibitors is associated with a better tolerability opened new horizons in the search of safer drugs for the management of inflammation. In the present study, we report the synthesis and the pharmacological evaluation of pyridine analogues of nimesulide, a COX-2 preferential inhibitor. The cyclooxygenases (COXs) inhibitory activities were evaluated in vitro using a human whole blood model. According to the in vitro results, a selection of compounds exhibiting moderate to high COX-2/COX-1 selectivity ratio (from weak COX-2 preferential inhibitors to compounds displaying a celecoxib-like selectivity profile) were further evaluated in vivo in a model of A carrageenan-induced pleurisy in rats. Some of the selected compounds displayed similar or improved anti-inflammatory properties when compared to nimesulide and celecoxib.

  DOI：

  10.1021/jm900702b

文献信息

• Pyridine Analogues of Nimesulide: Design, Synthesis, and in Vitro and in Vivo Pharmacological Evaluation as Promising Cyclooxygenase 1 and 2 Inhibitors
  作者：Jean-François Renard、Deniz Arslan、Nancy Garbacki、Bernard Pirotte、Xavier de Leval

  DOI：10.1021/jm900702b

  日期：2009.10.8

  Nonsteroidal anti-inflammatory drugs (NSAIDs) represent one of the most prescribed medications, although the chronic use of such pharmacological agents is commonly associated with numerous side effects. The demonstration that the use of COX-2 selective or preferential inhibitors is associated with a better tolerability opened new horizons in the search of safer drugs for the management of inflammation. In the present study, we report the synthesis and the pharmacological evaluation of pyridine analogues of nimesulide, a COX-2 preferential inhibitor. The cyclooxygenases (COXs) inhibitory activities were evaluated in vitro using a human whole blood model. According to the in vitro results, a selection of compounds exhibiting moderate to high COX-2/COX-1 selectivity ratio (from weak COX-2 preferential inhibitors to compounds displaying a celecoxib-like selectivity profile) were further evaluated in vivo in a model of A carrageenan-induced pleurisy in rats. Some of the selected compounds displayed similar or improved anti-inflammatory properties when compared to nimesulide and celecoxib.