5-(3-chlorophenyl)-1-phenyl-1H-1,2,3-triazole | 1378976-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-chlorophenyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 5-(3-Chlorophenyl)-1-phenyltriazole
• CAS: 1378976-17-0
• 化学式: C₁₄H₁₀ClN₃
• 分子量: 255.707
• InChiKey: DKPJRHWJUFPDTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯苯乙醇 在 硫酰氟 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 5-(3-chlorophenyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Transition-metal-free regioselective construction of 1,5-diaryl-1,2,3-triazoles through dehydrative cycloaddition of alcohols with aryl azides mediated by SO₂F₂

  摘要：

  开发了一种新颖、简单且实用的方法，用于高效、经济、具有区域选择性的合成高价值的1,5-二芳基-1,2,3-三唑。

  DOI：

  10.1039/c8cc09693g

文献信息

• Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition: Role of Er(OTf)3, ionic liquid and water
  作者：Loredana Maiuolo、Beatrice Russo、Vincenzo Algieri、Monica Nardi、Maria Luisa Di Gioia、Matteo Antonio Tallarida、Antonio De Nino

  DOI：10.1016/j.tetlet.2019.01.053

  日期：2019.2

  A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the Er(OTf)3/[mpy]OTf/H2O catalytic system is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regioselective approach and good yields (81–94%). The advantages of this method include simple operations of work-up and the ability of the catalytic system to be re-used five times

  描述了使用Er（OTf）3 / [mpy] OTf / H 2 O催化体系获得1,5-二取代的1,2,3-三唑的简单程序。该反应通过消除叠氮化物-烯烃环加成反应（EAOC）进行，提供了高度区域选择性的方法和良好的收率（81-94％）。该方法的优点包括后处理的简单操作以及催化体系可以重复使用五次而不会明显降低产率的能力。推测了IL和水的作用，还引起了可能的离子自组装（ISA）效应。
• Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Aurélien Grosdidier、Sylvian Bron、Vincent Stroobant、Luc Pilotte、Didier Colau、Pierre Vogel、Benoît J. Van den Eynde、Vincent Zoete、Olivier Michielin

  DOI：10.1021/jm300260v

  日期：2012.6.14

  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.