4-carboxamido-5-[N-(ethoxycarbonyl)-N-(4-fluoro-2-aminophenyl)]-amino-1,2,3-triazole | 328535-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-carboxamido-5-[N-(ethoxycarbonyl)-N-(4-fluoro-2-aminophenyl)]-amino-1,2,3-triazole
• 英文别名: ethyl N-(2-amino-4-fluorophenyl)-N-(5-carbamoyl-2H-triazol-4-yl)carbamate
• CAS: 328535-08-6
• 化学式: C₁₂H₁₃FN₆O₃
• 分子量: 308.272
• InChiKey: FDZWXTDJWPJWCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-carboxamido-5-[N-(ethoxycarbonyl)-N-(4-fluoro-2-aminophenyl)]-amino-1,2,3-triazole 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到5-(5-fluoro-2-oxo-3H-benzimidazol-1-yl)-2H-triazole-4-carboxamide
  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：

  4-carboxamido-5-[N-(ethoxycarbonyl)-N-(4-fluoro-2-nitrophenyl)]-amino-1,2,3-triazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到4-carboxamido-5-[N-(ethoxycarbonyl)-N-(4-fluoro-2-aminophenyl)]-amino-1,2,3-triazole
  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

文献信息

• 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.