3-[1-(3-Butoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[1-(3-Butoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid ethyl ester
• 英文别名: ethyl 3-[(E)-(3-butoxyphenyl)methylideneamino]oxypropanoate
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: ROLNIJCNWVVULN-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[1-(3-Butoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以20%的产率得到3-[1-(3-Butoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid
  参考文献：
  名称：

  Synthesis, antiinflammatory activity and molecular orbital studies of a series of benzylideneaminoxypropionic acids substituted on the phenyl ring

  摘要：

  An examination of the antiinflammatory properties of certain beta-aminoxypropionic acids A (AOPAs) previously synthe- sized as analogs of antiinflammatory drugs with an arylacetic structure B (ArAAs), indicated that the most active acid is the (E)-3-(benzylideneaminoxy)-propionic acid (1), which was found to possess an activity comparable to that of Diclofenac (8). In an attempt to verify whether appropriate substitutions on the aromatic ring of 1 can modulate the antiinflammatory properties of this class of drugs, a series of benzylideneaminoxypropionic acids (BAOPAs) were synthesized, in which the phenyl group is substituted, in its 3 possible positions, by groups possessing different electronic, steric, and lipophilic characteristics. The antiinflammatory activity of the new compounds was determined by carrageenan-induced rat paw edema, using Diclofenac (8) as the reference drug. The pharmacological results revealed that among the BAOPAs examined, the most active are the m-chloro (7b) and p-ethoxy (7p) substituted compounds, which exhibit an antiinflammatory activity comparable to that of 1. Quantum mechanical calculations were also carried out in order to gain insight into the possible correlations between the pharmacological activity observed and the electronic and conformational effects induced by the presence of the various substituents.

  DOI：

  10.1016/0223-5234(94)90123-6
• 作为产物：
  描述：

  3-Butoxy-benzaldehyde oxime 、 丙烯酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以70%的产率得到3-[1-(3-Butoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis, antiinflammatory activity and molecular orbital studies of a series of benzylideneaminoxypropionic acids substituted on the phenyl ring

  摘要：

  An examination of the antiinflammatory properties of certain beta-aminoxypropionic acids A (AOPAs) previously synthe- sized as analogs of antiinflammatory drugs with an arylacetic structure B (ArAAs), indicated that the most active acid is the (E)-3-(benzylideneaminoxy)-propionic acid (1), which was found to possess an activity comparable to that of Diclofenac (8). In an attempt to verify whether appropriate substitutions on the aromatic ring of 1 can modulate the antiinflammatory properties of this class of drugs, a series of benzylideneaminoxypropionic acids (BAOPAs) were synthesized, in which the phenyl group is substituted, in its 3 possible positions, by groups possessing different electronic, steric, and lipophilic characteristics. The antiinflammatory activity of the new compounds was determined by carrageenan-induced rat paw edema, using Diclofenac (8) as the reference drug. The pharmacological results revealed that among the BAOPAs examined, the most active are the m-chloro (7b) and p-ethoxy (7p) substituted compounds, which exhibit an antiinflammatory activity comparable to that of 1. Quantum mechanical calculations were also carried out in order to gain insight into the possible correlations between the pharmacological activity observed and the electronic and conformational effects induced by the presence of the various substituents.

  DOI：

  10.1016/0223-5234(94)90123-6