3-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)-1-methylquinolin-2(1H)-one | 1375313-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)-1-methylquinolin-2(1H)-one
• 英文别名: 3-[4-[4-(Dimethylamino)phenyl]triazol-1-yl]-1-methylquinolin-2-one
• CAS: 1375313-79-3
• 化学式: C₂₀H₁₉N₅O
• 分子量: 345.404
• InChiKey: QFBOZCCCIXYMHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-Azido-1-methylquinolin-2-one 、 4-二甲基氨基苯乙炔 在 噻吩-2-甲酸亚铜(I) 作用下， 以 乙醇 为溶剂， 以75%的产率得到3-(4-(4-(dimethylamino)phenyl)-1H-1,2,3-triazol-1-yl)-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and antikinetoplastid activities of 3-substituted quinolinones derivatives

  摘要：

  A new family of quinolinone derivatives has been synthesized and evaluated for their antikinetoplastid activities against Leishmania donovani and Trypanosoma brucei brucei. Results from these structure activity relationship studies enabled identification of compounds 3a and 4g as the most active compounds against L. donovani promastigotes and amastigotes parasites (IC50 values in a range of 2-11 mu M). Additionally, compound 3b has emerged from this study as the most active compound in the series against T. b. brucei with a MEC value of 12 mu M. These three compounds are worth of further in vivo evaluation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.003

文献信息

• An efficient synthesis of 3-triazolyl-2(1<i>H</i> )-quinolones by CuTC-catalyzed azide-alkyne cycloaddition reaction
  作者：Samir Messaoudi、Marie Gabillet、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1002/aoc.2946

  日期：2013.3

  A facile and efficient Cu(I)‐catalyzed azide–alkyne cycloaddition reaction for the synthesis of a series of 3‐triazolyl‐2(1H)‐quinolones 3 have been developed using 3‐azido‐quinolin‐2(1H)‐one as the coupling partner. The optimized reaction conditions involve the use of eco‐ friendly ethanol as the solvent in the presence of copper(I) thiophene‐2‐carboxylate as the catalyst, to afford good to excellent

  使用3-叠氮基-喹啉-2（1 H）-开发了一种简便高效的Cu（I）催化的叠氮化物-炔烃环加成反应，用于合成一系列3-triazolyl-2（1 H）-quinolones 3。一个作为耦合伙伴。优化的反应条件包括在噻吩-2-羧酸铜（I）存在下使用生态乙醇作为溶剂，以提供良好的3-三唑基-2（1 H）-喹诺酮收率具有生物意义的衍生物。版权所有©2013 John Wiley＆Sons，Ltd.
• Synthesis and antikinetoplastid activities of 3-substituted quinolinones derivatives
  作者：Davide Audisio、Samir Messaoudi、Sandrine Cojean、Jean-François Peyrat、Jean-Daniel Brion、Christian Bories、Françoise Huteau、Philippe M. Loiseau、Mouad Alami

  DOI：10.1016/j.ejmech.2012.03.003

  日期：2012.6

  A new family of quinolinone derivatives has been synthesized and evaluated for their antikinetoplastid activities against Leishmania donovani and Trypanosoma brucei brucei. Results from these structure activity relationship studies enabled identification of compounds 3a and 4g as the most active compounds against L. donovani promastigotes and amastigotes parasites (IC50 values in a range of 2-11 mu M). Additionally, compound 3b has emerged from this study as the most active compound in the series against T. b. brucei with a MEC value of 12 mu M. These three compounds are worth of further in vivo evaluation. (C) 2012 Elsevier Masson SAS. All rights reserved.