ethyl 1-(2-acetylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate | 1362020-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(2-acetylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
• CAS: 1362020-83-4
• 化学式: C₁₄H₁₅N₃O₃
• 分子量: 273.291
• InChiKey: NEVAHKPBXCDLNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.08
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  邻氨基苯乙酮 在 盐酸 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 1.17h， 生成 ethyl 1-(2-acetylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate 、 ethyl 1-(2-acetylphenyl)-4-methyl-1H-1,2,3-triazole-5-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Biological Evaluation of 1H-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein

  摘要：

  The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC50 values ranging from 0.5 to 4.6 mu M. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC50 values in sub-mu M ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.

  DOI：

  10.1021/jm2013503

文献信息

• Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐ <i>a</i> ]quinolines
  作者：Gabriel P. Costa、Mariana F. Bach、Maiara C. Moraes、Thiago Barcellos、Eder J. Lenardão、Márcio S. Silva、Diego Alves

  DOI：10.1002/adsc.202000887

  日期：2020.11.18

  organocatalytic method for the synthesis of fused [1,2,3]triazolo[1,5‐a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3+2]‐cycloaddition occurs between 1,3‐dicarbonyl compounds and o‐carbonyl‐substituted phenylazide compounds, for the formation of the 1,2,3‐triazole intermediates. Subsequently, an intramolecular condensation reaction

  在这项工作中，提出了一种通过连续环化和缩合反应合成稠合[1,2,3]三唑并[1,5- a ]喹啉的单锅顺序有机催化方法。在这种合成策略中，分子间的[3 + 2]-环加成反应发生在1,3-二羰基化合物与邻羰基取代的苯叠氮化合物之间，从而形成1,2,3-三唑中间体。随后，分子内的缩合反应通过新的C-C键的形成生成稠合的喹啉环，从而使产物的收率从中等到极好。在DMSO作为溶剂存在下，使用20 mol％的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为催化剂，在120°C下进行24 h，反应范围为1。 ，3-二羰基化合物，例如β-酮酸酯和1,3-二酮，以及邻甲酰基，邻乙酰基或邻苯甲酰基取代的苯叠氮化合物。