4-carboxamido-5-(4-sec-butyl-2-aminoanilino)-1,2,3-triazole | 304874-20-2

• 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-(4-sec-butyl-2-aminoanilino)-1,2,3-triazole
• 英文别名: 5-(2-amino-4-butan-2-ylanilino)-2H-triazole-4-carboxamide
• CAS: 304874-20-2
• 化学式: C₁₃H₁₈N₆O
• 分子量: 274.326
• InChiKey: RYMAZWILKSJZOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-carboxamido-5-(4-sec-butyl-2-aminoanilino)-1,2,3-triazole 在 盐酸 、 sodium nitrite 作用下， 反应 2.33h， 以66%的产率得到1-(5-carboxamido-1,2,3-triazol-4-yl)-5-sec-butylbenzotriazole
  参考文献：
  名称：

  三唑基-苯并三唑和三唑基-苯并咪唑啉酮作为潜在的钾通道活化剂的一些结构变化。三，

  摘要：

  本文报道了通过1,2,3-三唑基-苯并三唑和1,2,3-三唑基-苯并咪唑啉酮的结构修饰获得的一些化合物的合成和药理学评价，这些化合物已显示出作为大电导钙的潜在活化剂的活性。激活的钾离子通道（BK（Ca））。变化涉及在苯并咪唑酮（4a，b）和苯并三唑（5a，b）环的5位引入阻位取代基，苯并咪唑酮环（7）的开环和1,2,3-三唑的取代环带有2-羟基苯基环（10）。此外，已经研究了一系列3-芳基-苯并三嗪-4-酮衍生物（13a-e），其表现为苯并咪唑酮和苯并三唑环的修饰和/或组合。只有化合物10显示出有趣的活性，而其他结构修饰不会增加（化合物4和5）或降低（化合物7和13）药理活性。但是，这些结果提供了有关结构-活性关系的有用信息。

  DOI：

  10.1016/s0014-827x(01)01148-x
• 作为产物：
  描述：

  (+/-)-4-sec-Butyl-acetanilid 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 硫酸 、 氢气 、 硝酸 、 sodium ethanolate 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， -10.0~50.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 4-carboxamido-5-(4-sec-butyl-2-aminoanilino)-1,2,3-triazole
  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

• Some structural changes on triazolyl-benzotriazoles and triazolyl-benzimidazolones as potential potassium channel activators. III
  作者：Giuliana Biagi、Vincenzo Calderone、Irene Giorgi、Oreste Livi、Valerio Scartoni、Barbara Baragatti、Enrica Martinotti

  DOI：10.1016/s0014-827x(01)01148-x

  日期：2001.11

  (4a, b) and benzotriazole (5a, b) rings, opening of the benzimidazolone ring (7) and substitution of the 1,2,3-triazole ring with a 2-hydroxyphenyl ring (10). Furthermore a series of 3-aryl-benzotriazin-4-one derivatives (13a-e) has been studied, which appears as a modification and/or combination of the benzimidazolone and benzotriazole rings. Only compound 10 shows interesting activity, while the other

  本文报道了通过1,2,3-三唑基-苯并三唑和1,2,3-三唑基-苯并咪唑啉酮的结构修饰获得的一些化合物的合成和药理学评价，这些化合物已显示出作为大电导钙的潜在活化剂的活性。激活的钾离子通道（BK（Ca））。变化涉及在苯并咪唑酮（4a，b）和苯并三唑（5a，b）环的5位引入阻位取代基，苯并咪唑酮环（7）的开环和1,2,3-三唑的取代环带有2-羟基苯基环（10）。此外，已经研究了一系列3-芳基-苯并三嗪-4-酮衍生物（13a-e），其表现为苯并咪唑酮和苯并三唑环的修饰和/或组合。只有化合物10显示出有趣的活性，而其他结构修饰不会增加（化合物4和5）或降低（化合物7和13）药理活性。但是，这些结果提供了有关结构-活性关系的有用信息。
• 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.