N,N-dimethyl-2-(6-methyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetamide | 26509-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N,N-dimethyl-2-(6-methyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetamide
• 英文别名: N,N-Dimethyl-2-(6-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-YL)acetamide；N,N-dimethyl-2-(6-methyl-3-oxo-1,4-benzoxazin-4-yl)acetamide
• CAS: 26509-11-5
• 化学式: C₁₃H₁₆N₂O₃
• mdl: MFCD04205951
• 分子量: 248.282
• InChiKey: HGRLVTOZJWZAPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-N-(2-hydroxy-5-methylphenyl)acetamide 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N,N-dimethyl-2-(6-methyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetamide
  参考文献：
  名称：

  Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators

  摘要：

  With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80020-8

文献信息

• Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators
  作者：Giuseppe Caliendo、Paolo Grieco、Elisa Perissutti、Vincenzo Santagada、Antonello Santini、Stefania Albrizio、Caterina Fattorusso、Aldo Pinto、Raffaella Sorrentino

  DOI：10.1016/s0223-5234(99)80020-8

  日期：1998.12

  With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug. (C) Elsevier, Paris.