3-phenoxypyridine-4-carboxylic acid 1-oxide | 112945-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenoxypyridine-4-carboxylic acid 1-oxide
• 英文别名: 1-Oxido-3-phenoxypyridin-1-ium-4-carboxylic acid
• CAS: 112945-96-7
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: GJEKFQGWFKIMRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-phenoxyisonicotinic acid 在 过氧乙酸 作用下， 以85%的产率得到3-phenoxypyridine-4-carboxylic acid 1-oxide
  参考文献：
  名称：

  3-Phenoxypyridine 1-oxides as anticonvulsant agents

  摘要：

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.

  DOI：

  10.1021/jm00399a027

文献信息

• PAVIA, MICHAEL R.;TAYLOR, CHARLES P.;HERSHENSON, FRED M.;LOBBESTAEL, SAND+, J. MED. CHEM., 31,(1988) N 4, 841-847
  作者：PAVIA, MICHAEL R.、TAYLOR, CHARLES P.、HERSHENSON, FRED M.、LOBBESTAEL, SAND+

  DOI：——

  日期：——
• 3-Phenoxypyridine 1-oxides as anticonvulsant agents
  作者：Michael R. Pavia、Charles P. Taylor、Fred M. Hershenson、Sandra J. Lobbestael、Donald E. Butler

  DOI：10.1021/jm00399a027

  日期：1988.4

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.