2-乙基-3-氧代吲唑-1-羧酸乙酯 | 89438-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 2-乙基-3-氧代吲唑-1-羧酸乙酯
• 英文名称: Ethyl 2-ethyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate
• 英文别名: ethyl 2-ethyl-3-oxoindazole-1-carboxylate
• CAS: 89438-41-5
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: XAYKKKLPKFDLDU-UHFFFAOYSA-N

物化性质

• 沸点：
  340.7±25.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙基-3-氧代吲唑-1-羧酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到2-ethyl-1H-indazol-3(2H)-one
  参考文献：
  名称：

  Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs

  摘要：

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.

  DOI：

  10.1021/jm00372a011
• 作为产物：
  描述：

  3-羟基-1H-吲唑 在 吡啶 、 氢氧化钾 作用下， 反应 12.0h， 生成 2-乙基-3-氧代吲唑-1-羧酸乙酯
  参考文献：
  名称：

  Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs

  摘要：

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.

  DOI：

  10.1021/jm00372a011

文献信息

• Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs
  作者：Steven D. Wyrick、P. Josee Voorstad、George Cocolas、Iris H. Hall

  DOI：10.1021/jm00372a011

  日期：1984.6

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.