5-(2-amino-4-fluoroanilino)-2H-triazole-4-carboxamide | 304874-18-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(2-amino-4-fluoroanilino)-2H-triazole-4-carboxamide
• CAS: 304874-18-8
• 化学式: C₉H₉FN₆O
• 分子量: 236.208
• InChiKey: ZQYQYHVOIYAPCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-amino-4-fluoroanilino)-2H-triazole-4-carboxamide 在 盐酸 、 sodium nitrite 作用下， 反应 1.33h， 以78%的产率得到5-(5-Fluoro-benzotriazol-1-yl)-1H-[1,2,3]triazole-4-carboxylic acid amide
  参考文献：
  名称：

  Triazolyl–benzimidazolones and triazolyl–benzotriazoles: new potential potassium channel activators. II

  摘要：

  This paper reports the synthesis and pharmacological evaluation of a series of 5-substituted-triazolyl-benzotriazoles (2a-f) and the corresponding series of 5-substituted-triazolyl-benzimidazolones (6a-f), as potential activators of the big-conductance calcium-activated potassium channels (BKCa). The synthesis and structure demonstration of the stock compounds of the two series have been described in our previous works, as well as the common starting compounds 4-carboxamido-5-(4-substituted-2-amino-anilino)-1,2,3-triazoles (1a-f). The triazolyl-benzotriazoles were obtained by diazotization, while the triazolyl-benzimida-zolones were obtained by thermal intramolecular cyclization of ethoxycarbonylamino derivatives or directly with phosgene. Benzimidazolone compounds generally showed little effect whilst the compounds with a benzotriazole ring showed full efficacy, with vasorelaxing properties and potency parameters a little lower than that of the reference compound NS 1619. These effects were significantly reduced by an increased membrane depolarization. This depolarization-sensitive response is in agreement with the pharmacodynamic hypothesis of activation of potassium channels. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01170-3
• 作为产物：
  描述：

  5-(4-fluoro-2-nitroanilino)-2H-triazole-4-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以84%的产率得到5-(2-amino-4-fluoroanilino)-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

文献信息

• 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.
• Triazolyl–benzimidazolones and triazolyl–benzotriazoles: new potential potassium channel activators. II
  作者：Barbara Baragatti、Giuliana Biagi、Vincenzo Calderone、Irene Giorgi、Oreste Livi、Enrica Martinotti、Valerio Scartoni

  DOI：10.1016/s0223-5234(00)01170-3

  日期：2000.10

  This paper reports the synthesis and pharmacological evaluation of a series of 5-substituted-triazolyl-benzotriazoles (2a-f) and the corresponding series of 5-substituted-triazolyl-benzimidazolones (6a-f), as potential activators of the big-conductance calcium-activated potassium channels (BKCa). The synthesis and structure demonstration of the stock compounds of the two series have been described in our previous works, as well as the common starting compounds 4-carboxamido-5-(4-substituted-2-amino-anilino)-1,2,3-triazoles (1a-f). The triazolyl-benzotriazoles were obtained by diazotization, while the triazolyl-benzimida-zolones were obtained by thermal intramolecular cyclization of ethoxycarbonylamino derivatives or directly with phosgene. Benzimidazolone compounds generally showed little effect whilst the compounds with a benzotriazole ring showed full efficacy, with vasorelaxing properties and potency parameters a little lower than that of the reference compound NS 1619. These effects were significantly reduced by an increased membrane depolarization. This depolarization-sensitive response is in agreement with the pharmacodynamic hypothesis of activation of potassium channels. (C) 2000 Editions scientifiques et medicales Elsevier SAS.