5-Amino-1-(4-methyl-2-nitrophenyl)triazole-4-carboxamide | 187840-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Amino-1-(4-methyl-2-nitrophenyl)triazole-4-carboxamide
• CAS: 187840-69-3
• 化学式: C₁₀H₁₀N₆O₃
• 分子量: 262.228
• InChiKey: ZYPFYCVUDZYCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Amino-1-(4-methyl-2-nitrophenyl)triazole-4-carboxamide 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 5-(2-amino-4-methylanilino)-2H-triazole-4-carboxamide
  参考文献：
  名称：

  5-(4′-Substituted-2′-nitroanilino)-1,2,3-triazoles as new potential potassium channel activators. I

  摘要：

  By the hypothesised correlation with the large conductance Ca++-activated potassium channel (BKCa) openers NS 004 and NS 1619, bearing a benzimidazolone ring, a series of new 5-(4'-substituted-2'-nitroanilino)-1,2,3-triazoles were synthesised and tested on in vitro isolated vascular preparation. The compounds were prepared. starting from the appropriately substituted 2-nitro-phenylazides by 1,3-dipolar cycloaddition reaction to cyanoacetamide and following Dimroth isomerisation of the corresponding 1-arylsubstituted-5-amino-1,2,3-triazoles. The analogous 5-(4'-substituted-2'-amino-anilino)-1,2,3-triazoles were also prepared to assess the role of the nitro group in the pharmacophoric model. Almost all the nitro compounds showed a vasorelaxant activity on endothelium-denuded rat aortic rings with a potency comparable to that recorded for the reference compound NS 1619. Such a vasorelaxing activity was significantly reduced by the increase of the level of membrane depolarisation and by the potassium channel blocker 4-aminopyridine with a pharmacodynamic behaviour consistent with a potassium channel activation. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00180-x
• 作为产物：
  描述：

  1-叠氮基-4-甲基-2-硝基苯 、 氰乙酰胺 在 sodium ethanolate 作用下， 生成 5-Amino-1-(4-methyl-2-nitrophenyl)triazole-4-carboxamide
  参考文献：
  名称：

  新的4-（苯并三唑-1-基）-1,2,3-三唑衍生物

  摘要：

  通过1-（2-氨基苯基）-4-羧酰胺基-5-氨基-1 H -1的重氮化反应获得新的4-（苯并三唑-1-基）-1，2，3-三唑结构， 2,3-三唑（1c）或相应的Dimroth异构体1d。它经历了一些常见的反应，以评估其化学行为和结构。从2-硝基-4-甲基苯基叠氮化物进行类似的反应序列，以将结构赋予所制备的硝基衍生物。通过化学和光谱方法证实了所制备的新化合物的结构。

  DOI：

  10.1002/jhet.5570330648

文献信息

• New 4-(benzotriazol-1-yl)-1,2,3-triazole derivatives
  作者：Gialiana Biagi、Irene Giorgi、Oreste Livi、Valerio Scartoni、Silvia Velo、Pier Luigi Barili

  DOI：10.1002/jhet.5570330648

  日期：1996.11

  A new 4-(benzotriazol-1-yl)-1,2,3-triazole structure was obtained by the diazotization reaction of either of 1-(2-aminophenyl)-4-carboxamido-5-amino-1H-1,2,3-triazole (1c) or of the corresponding Dimroth isomer 1d. It underwent some common reactions to evaluate its chemical behaviour and structure. An analogous reaction sequence was carried out from the 2-nitro-4-methylphenyl azide, to assign the structure

  通过1-（2-氨基苯基）-4-羧酰胺基-5-氨基-1 H -1的重氮化反应获得新的4-（苯并三唑-1-基）-1，2，3-三唑结构， 2,3-三唑（1c）或相应的Dimroth异构体1d。它经历了一些常见的反应，以评估其化学行为和结构。从2-硝基-4-甲基苯基叠氮化物进行类似的反应序列，以将结构赋予所制备的硝基衍生物。通过化学和光谱方法证实了所制备的新化合物的结构。
• 5-(4′-Substituted-2′-nitroanilino)-1,2,3-triazoles as new potential potassium channel activators. I
  作者：Giuliana Biagi、Vincenzo Calderone、Irene Giorgi、Oreste Livi、Valerio Scartoni、Barbara Baragatti、Enrica Martinotti

  DOI：10.1016/s0223-5234(00)00180-x

  日期：2000.8

  By the hypothesised correlation with the large conductance Ca++-activated potassium channel (BKCa) openers NS 004 and NS 1619, bearing a benzimidazolone ring, a series of new 5-(4'-substituted-2'-nitroanilino)-1,2,3-triazoles were synthesised and tested on in vitro isolated vascular preparation. The compounds were prepared. starting from the appropriately substituted 2-nitro-phenylazides by 1,3-dipolar cycloaddition reaction to cyanoacetamide and following Dimroth isomerisation of the corresponding 1-arylsubstituted-5-amino-1,2,3-triazoles. The analogous 5-(4'-substituted-2'-amino-anilino)-1,2,3-triazoles were also prepared to assess the role of the nitro group in the pharmacophoric model. Almost all the nitro compounds showed a vasorelaxant activity on endothelium-denuded rat aortic rings with a potency comparable to that recorded for the reference compound NS 1619. Such a vasorelaxing activity was significantly reduced by the increase of the level of membrane depolarisation and by the potassium channel blocker 4-aminopyridine with a pharmacodynamic behaviour consistent with a potassium channel activation. (C) 2000 Editions scientifiques et medicales Elsevier SAS.