4-chloro-3-phenoxypyridine | 73406-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-3-phenoxypyridine
• CAS: 73406-90-3
• 化学式: C₁₁H₈ClNO
• 分子量: 205.644
• InChiKey: OAFJWUWAKXLAMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-3-phenoxypyridine 在 过氧乙酸 作用下， 以25%的产率得到4-chloro-3-phenoxypyridine 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
• 作为产物：
  描述：

  3-phenoxypyridine 1-oxide 在 三氯氧磷 作用下， 反应 4.0h， 以3%的产率得到2-chloro-3-phenoxypyridine
  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

• 3-Aryloxy-substituted-aminopyridines and methods for their production
  申请人：Warner-Lambert Company

  公开号：US04179563A1

  公开（公告）日：1979-12-18

  3-Aryloxy-substituted-aminopyridines and salts thereof, which are useful as pharmacological agents, especially cognition activators, are disclosed. They can be produced by reacting a chloro-3-aryloxypyridine with a substituted amine, 3-bromo-substituted-aminopyridine with an alkali metal salt of a phenol compound or by deoxygenation of a 3-aryloxy-substituted-aminopyridine N-oxide.

  本文披露了作为药理活性剂特别是认知活化剂有用的3-芳氧基取代氨基吡啶及其盐。它们可通过将氯-3-芳氧基吡啶与取代胺反应、3-溴取代氨基吡啶与酚化合物的碱金属盐反应，或者通过脱氧化3-芳氧基取代氨基吡啶N-氧化物来制备。
• 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：——
• US4179563A
  申请人：——

  公开号：US4179563A

  公开（公告）日：1979-12-18
• 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.