4-methyl-3-(1H-1,2,3-triazol-4-yl)aniline | 1378976-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-3-(1H-1,2,3-triazol-4-yl)aniline
• 英文别名: 4-methyl-3-(2H-triazol-4-yl)aniline
• CAS: 1378976-11-4
• 化学式: C₉H₁₀N₄
• 分子量: 174.205
• InChiKey: WDCOUVGIAXUSJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙炔-4-甲基苯胺 在 copper(l) iodide 、 叠氮基三甲基硅烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到4-methyl-3-(1H-1,2,3-triazol-4-yl)aniline
  参考文献：
  名称：

  Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

  DOI：

  10.1021/jm300260v