5-ethyl-1-(3-phenyl-2,1-benzisoxazol-5-yl)-1H-1,2,3-triazole-4-carboxylic acid | 1017426-83-3

• 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: 5-ethyl-1-(3-phenyl-2,1-benzisoxazol-5-yl)-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 5-ethyl-1-(3-phenyl-2,1-benzoxazol-5-yl)triazole-4-carboxylic acid
• CAS: 1017426-83-3
• 化学式: C₁₈H₁₄N₄O₃
• mdl: MFCD10006367
• 分子量: 334.334
• InChiKey: KZCVJYGBQMOHHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-ethyl-1-(3-phenyl-2,1-benzisoxazol-5-yl)-1H-1,2,3-triazole-4-carboxylic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 N-(2-chlorophenyl)-5-ethyl-1-(3-phenyl-2,1-benzoxazol-5-yl)-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives

  摘要：

  Anticancer screening of several novel 1,2,3-triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide access to triazole derivatives production. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. It was observed that some compounds showed remarkable anticancer activity. Two of them possessed a significant activity on leukemia, melanoma, non-small cell lung, CNS, ovarian, renal, and breast cancer. 5-Amino-1-p-tolyl-1H-[1,2,3]triazole-4-carboxylic acid (2,5-dichloro-phenyl)-amide showed a significant correlation in COMPARE analysis.1,2,3-triazole-4-carboxamide derivatives were synthesized in a simple and convenient synthetic path, their in vitro anticancer activity was examined after the performance of molecular docking.

  DOI：

  10.1007/s00044-013-0841-8
• 作为产物：
  描述：

  5-ethyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid 、 苯乙腈 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 28.0h， 以88%的产率得到5-ethyl-1-(3-phenyl-2,1-benzisoxazol-5-yl)-1H-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  氢在亲氮环上活化的硝基芳烃中亲核取代氢合成2,1-苯并异恶唑

  摘要：

  1-硝基-4-（1,2,3-三唑基/四唑基）苯与芳基乙腈在酒精介质中在过量碱存在下的反应产生了新的2,1-苯并恶唑。这些发现表明由于它们的电子缺陷特性，被唑环活化的硝基芳烃具有高反应活性。此外，发现在二取代的硝基芳烃中区域选择性地发生异恶唑环的环化。在1-（4-硝基苯基）-1-的情况下ħ四唑，四唑环裂解比σ更快ħ形成-adduct。 1 H -1,2,3-三唑-四唑-亲核取代-2,1-苯并恶唑-环化

  DOI：

  10.1055/s-0029-1216875

文献信息

• Synthesis of 2,1-Benzisoxazoles by Nucleophilic Substitution of Hydrogen in Nitroarenes Activated by the Azole Ring
  作者：Nazariy Pokhodylo、Yuriy Teslenko、Vasyl Matiychuk、Mykola Obushak

  DOI：10.1055/s-0029-1216875

  日期：——

  nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the σH-adduct was formed. 1H-1,2,3-triazole - tetrazole - nucleophilic substitution - 2,1-benzisoxazole - annulation

  1-硝基-4-（1,2,3-三唑基/四唑基）苯与芳基乙腈在酒精介质中在过量碱存在下的反应产生了新的2,1-苯并恶唑。这些发现表明由于它们的电子缺陷特性，被唑环活化的硝基芳烃具有高反应活性。此外，发现在二取代的硝基芳烃中区域选择性地发生异恶唑环的环化。在1-（4-硝基苯基）-1-的情况下ħ四唑，四唑环裂解比σ更快ħ形成-adduct。 1 H -1,2,3-三唑-四唑-亲核取代-2,1-苯并恶唑-环化
• Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives
  作者：Nazariy Pokhodylo、Olga Shyyka、Vasyl Matiychuk

  DOI：10.1007/s00044-013-0841-8

  日期：2014.5

  Anticancer screening of several novel 1,2,3-triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide access to triazole derivatives production. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. It was observed that some compounds showed remarkable anticancer activity. Two of them possessed a significant activity on leukemia, melanoma, non-small cell lung, CNS, ovarian, renal, and breast cancer. 5-Amino-1-p-tolyl-1H-[1,2,3]triazole-4-carboxylic acid (2,5-dichloro-phenyl)-amide showed a significant correlation in COMPARE analysis.1,2,3-triazole-4-carboxamide derivatives were synthesized in a simple and convenient synthetic path, their in vitro anticancer activity was examined after the performance of molecular docking.