4-amino-3-(4-methoxyphenoxy)pyridine | 132038-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-3-(4-methoxyphenoxy)pyridine
• 英文别名: 3-(4-methoxyphenoxy)-4-pyridinamine；3-(4-Methoxyphenoxy)pyridin-4-amine
• CAS: 132038-24-5
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: VXAGJGANWCAHIB-UHFFFAOYSA-N

物化性质

• 沸点：
  375.9±37.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-3-(4-methoxyphenoxy)pyridine 在 sodium hydroxide 、 双氧水 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成
  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related to the antiinflammatory and antihistaminic agent nimesulide (I), in which the p-nitrophenyl moiety has been replaced by pyridine (1a-c) and pyridine N-oxide (2a-c).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：

  3-溴吡啶 在 硫酸 、 potassium tert-butylate 、 双氧水 、 硝酸 、 铁粉 、 溶剂黄146 作用下， 以 叔丁醇 为溶剂， 反应 10.5h， 生成 4-amino-3-(4-methoxyphenoxy)pyridine
  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related to the antiinflammatory and antihistaminic agent nimesulide (I), in which the p-nitrophenyl moiety has been replaced by pyridine (1a-c) and pyridine N-oxide (2a-c).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

文献信息

• Phenoxypyridinamine compounds which are use as a dermatological
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04959377A1

  公开（公告）日：1990-09-25

  There are described compounds of the formula ##STR1## where n is 0 or 1; X is hydrogen, loweralkyl, loweralkoxy, halogen, formyl, loweralkylcarbonyl, loweralkyoxycarbonyl, loweralkoxycarbonylloweralkyl or hydroxymethyl; Y is hydrogen or halogen;and R is hydrogen, loweralkyl arylloweralkyl or loweralkylcarbonyl, which compounds are useful as topical antiinflammatory agents for the treatment of various dermatoses.

  描述了一种化合物，其化学式为##STR1##其中n为0或1；X为氢、较低的烷基、较低的烷氧基、卤素、甲酰基、较低的烷基羰基、较低的烷氧羰基、较低的烷氧羰基较低的烷基或羟甲基；Y为氢或卤素；R为氢、较低的烷基芳基较低的烷基或较低的烷基羰基，这些化合物可用作治疗各种皮肤病的局部抗炎药。
• Phenoxypyridinamines and related compounds, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0405487A1

  公开（公告）日：1991-01-02

  The present invention relates to compounds of the formula where n is 0 or 1; X is hydrogen, loweralkyl, loweralkoxy, halogen, formyl, loweralkylcarbonyl, loweralkoxycarbonyl, loweralkoxycarbonylloweralkyl or hydroxymethyl; Y is hydrogen or halogen; Z is NO₂ or NHR, were R is hydrogen, loweralkyl, arylloweralkyl or loweralkylcarbonyl, and to a process for their preparation. The compounds are useful as topical antiinflammatory agents for the treatment of various dermatoses.

  本发明涉及式如下的化合物 式中 n 是 0 或 1； X是氢、低级烷基、低级烷氧基、卤素、甲酰基、低级烷基羰基、低级烷氧基羰基、低级烷氧基羰基低级烷基或羟甲基； Y 是氢或卤素 Z 是 NO₂ 或 NHR，其中 R 是氢、低级烷基、芳基低级烷基或低级烷基羰基、 及其制备工艺。这些化合物可用作治疗各种皮肤病的局部消炎剂。
• Design, Synthesis, and Pharmacological Evaluation of Pyridinic Analogues of Nimesulide as Cyclooxygenase-2 Selective Inhibitors
  作者：Fabien Julémont、Xavier de Leval、Catherine Michaux、Jean-François Renard、Jean-Yves Winum、Jean-Louis Montero、Jacques Damas、Jean-Michel Dogné、Bernard Pirotte

  DOI：10.1021/jm049480l

  日期：2004.12.1

  In this study, we report the synthesis and pharmacological evaluation of original pyridinic sulfonamides related to nimesulide, a cyclooxygenase-2 (COX-2) preferential inhibitor widely used as an anti-inflammatory agent. These original pyridinic derivatives were synthesized in three steps starting from the condensation of 3-bromo-4-nitropyridine N-oxide with appropriately substituted phenols, thiophenols, or anilines followed by a reduction of the nitro moiety into the corresponding aminopyridine, which was finally condensed with alkane- or trifluoromethanesulfonyl chloride to obtain the corresponding sulfonamides. The pK(a) determinations demonstrated that the major ionic form present in solution at physiological pH depends on the nature of the sulfonamide moiety subsituent. Indeed, alkanesulfonamides were mainly present as zwitterionic molecules while trifluoromethanesulfonamides, more acidic derivatives, were mainly present as anionic molecules. The in vitro pharmacological evaluation of the synthesized compounds against COX-1 and COX-2 was performed in a human whole blood model. Results obtained demonstrated that most of alkanesulfonamide derivatives displayed a COX-2 preferential inhibition with selectivity ratio values (IC50(COX-1)/IC50(COX-2)) up to 7.92 (celecoxib displaying a ratio value of 7.46 in the same test). On the other hand, trifluoromethanesulfonamide derivatives displayed weaker selectivity ratios although they exhibited IC50 values against COX-2 up to 0.09 muM (celecoxib IC50 against COX-2: 0.35 muM). Finally, in vivo evaluation of selected compounds showed that they exhibited anti-inflammatory properties similar to that of nimesulide when tested in a carrageenan-induced rat paw oedema model.
• US4959377A
  申请人：——

  公开号：US4959377A

  公开（公告）日：1990-09-25