N-(3-苯氧基吡啶-4-基)甲磺酰胺 | 180194-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-(3-苯氧基吡啶-4-基)甲磺酰胺
• 英文名称: N-(3-phenoxy-4-pyridyl)methanesulfonamide
• 英文别名: N-(3-phenoxypyridin-4-yl)methanesulfonamide
• CAS: 180194-78-9
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: CQEDUEBRINEBGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-苯氧基吡啶-4-基)甲磺酰胺 在 双氧水 、 溶剂黄146 作用下， 反应 8.0h， 以47%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related to the antiinflammatory and antihistaminic agent nimesulide (I), in which the p-nitrophenyl moiety has been replaced by pyridine (1a-c) and pyridine N-oxide (2a-c).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 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 N-(3-苯氧基吡啶-4-基)甲磺酰胺
  参考文献：
  名称：

  Spectral and Crystallographic Study of Pyridinic Analogues of Nimesulide: Determination of the Active Form of Methanesulfonamides as COX-2 Selective Inhibitors

  摘要：

  Compound 7, N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide, showed in vitro (whole blood assay) a strong inhibitory activity on the two cyclooxygenase (COX) enzymes (IC50(COX-1) = 2.2 muM and IC50(COX-2) = 0.4 muM), being more active but less COX-2-selective than nimesulide. Physicochemical studies and structural analyses indicated that the anionic sulfonamidate species seemed to be the active form of methanesulfonamides, which optimally interacted with the COX enzymes' active sites.

  DOI：

  10.1021/jm020920n

文献信息

• Synthesis and pharmacological evaluation of derivatives structurally related to nimesulide
  作者：G Cignarella、P Vianello、F Berti、G Rossoni

  DOI：10.1016/0223-5234(96)89162-8

  日期：1996.1

  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.
• Spectral and Crystallographic Study of Pyridinic Analogues of Nimesulide: Determination of the Active Form of Methanesulfonamides as COX-2 Selective Inhibitors
  作者：Fabien Julémont、Xavier de Leval、Catherine Michaux、Jacques Damas、Caroline Charlier、François Durant、Bernard Pirotte、Jean-Michel Dogné

  DOI：10.1021/jm020920n

  日期：2002.11.1

  Compound 7, N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide, showed in vitro (whole blood assay) a strong inhibitory activity on the two cyclooxygenase (COX) enzymes (IC50(COX-1) = 2.2 muM and IC50(COX-2) = 0.4 muM), being more active but less COX-2-selective than nimesulide. Physicochemical studies and structural analyses indicated that the anionic sulfonamidate species seemed to be the active form of methanesulfonamides, which optimally interacted with the COX enzymes' active sites.