4-amino-3-phenoxypyridine-N-oxide | 180194-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-3-phenoxypyridine-N-oxide
• CAS: 180194-87-0
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: VOQKNVBGGKNUEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-amino-3-phenoxypyridine-N-oxide 以 乙腈 为溶剂， 反应 15.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of derivatives structurally related to nimesulide

  摘要：

  The present work reports the synthesis of a series of compounds structurally related to the antiinflammatory and antihistaminic agent nimesulide (I), in which the p-nitrophenyl moiety has been replaced by pyridine (1a-c) and pyridine N-oxide (2a-c). In addition, two compounds (3a, 4a) have been synthesized in which the p-nitro group of I was substituted by a cyano and a 1H-tetrazol-5-yl group, respectively. Representative 1a and 2a were also modified by replacing the methanesulfonamido group with an acetamido group (5a, 6a). The pharmacological evaluation of compounds 1-6 in comparison to I, indicates that such modifications are detrimental to the activity. Moreover 3a and 4a caused bronchoconstriction and hypotension, thus behaving as histaminic-like rather then antihistaminic agents.

  DOI：

  10.1016/0223-5234(96)89162-8
• 作为产物：
  描述：

  4-硝基-3-苯氧基吡啶N-氧化物 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以88%的产率得到4-amino-3-phenoxypyridine-N-oxide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of derivatives structurally related to nimesulide

  摘要：

  The present work reports the synthesis of a series of compounds structurally related to the antiinflammatory and antihistaminic agent nimesulide (I), in which the p-nitrophenyl moiety has been replaced by pyridine (1a-c) and pyridine N-oxide (2a-c). In addition, two compounds (3a, 4a) have been synthesized in which the p-nitro group of I was substituted by a cyano and a 1H-tetrazol-5-yl group, respectively. Representative 1a and 2a were also modified by replacing the methanesulfonamido group with an acetamido group (5a, 6a). The pharmacological evaluation of compounds 1-6 in comparison to I, indicates that such modifications are detrimental to the activity. Moreover 3a and 4a caused bronchoconstriction and hypotension, thus behaving as histaminic-like rather then antihistaminic agents.

  DOI：

  10.1016/0223-5234(96)89162-8