3-phthalimido-N-methyl-N-phenylpropionamide | 335207-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-phthalimido-N-methyl-N-phenylpropionamide
• 英文别名: 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-methyl-N-phenyl-propionamide；3-(1,3-dioxoisoindol-2-yl)-N-methyl-N-phenylpropanamide
• CAS: 335207-99-3
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: STOCVYFFHPYZER-UHFFFAOYSA-N

物化性质

• 溶解度：
  36.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phthalimido-N-methyl-N-phenylpropionamide 在 水 、 肼 作用下， 以 乙醇 为溶剂， 生成 3-amino-N-methyl-N-phenylpropanamide
  参考文献：
  名称：

  Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H₄ Receptor Inverse Agonists

  摘要：

  Hit optimization of the class of quinazoline containing histamine H-4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline-4-amino)-N-phenylethanesulfonamide (54) (pK(i) = 8.31 +/- 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.

  DOI：

  10.1021/jm901379s
• 作为产物：
  描述：

  1,3-二氢-1,3-二氧代-2H-异吲哚-2-丙酰氯 、 N-甲基苯胺 以 氯仿 为溶剂， 以3.38 g的产率得到3-phthalimido-N-methyl-N-phenylpropionamide
  参考文献：
  名称：

  Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H₄ Receptor Inverse Agonists

  摘要：

  Hit optimization of the class of quinazoline containing histamine H-4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline-4-amino)-N-phenylethanesulfonamide (54) (pK(i) = 8.31 +/- 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.

  DOI：

  10.1021/jm901379s