4-((4-((4-chlorophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-((4-((4-chlorophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl-2H-chromen-2-one
• 英文别名: 4-[[4-[(4-Chlorophenoxy)methyl]triazol-1-yl]methyl]-6-methylchromen-2-one；4-[[4-[(4-chlorophenoxy)methyl]triazol-1-yl]methyl]-6-methylchromen-2-one
• 化学式: C₂₀H₁₆ClN₃O₃
• 分子量: 381.818
• InChiKey: NIFQSQFCKZAGBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-methyl-4-bromomethylcoumarin 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 10.0h， 生成 4-((4-((4-chlorophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl-2H-chromen-2-one
  参考文献：
  名称：

  A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents

  摘要：

  A series of mono and bis-triazole coumarin hybrids 6a-u and 9a-f respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5a-i and aryl propargyl ethers 2a-c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a-u with MIC 50-100 mu g/mL, whereas the bis compounds 9a-f were more effective with MICs between 0.2 and 12.5 mu g/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The his compound 9b showed excellent activity with MIC value as low as 0.2 mu g/mL. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.019

文献信息

• A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents
  作者：Ashish Anand、Reshma J. Naik、Hrishikesh M. Revankar、Manohar V. Kulkarni、Sheshagiri R. Dixit、Shrinivas D. Joshi

  DOI：10.1016/j.ejmech.2015.10.019

  日期：2015.11

  A series of mono and bis-triazole coumarin hybrids 6a-u and 9a-f respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5a-i and aryl propargyl ethers 2a-c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a-u with MIC 50-100 mu g/mL, whereas the bis compounds 9a-f were more effective with MICs between 0.2 and 12.5 mu g/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The his compound 9b showed excellent activity with MIC value as low as 0.2 mu g/mL. (C) 2015 Elsevier Masson SAS. All rights reserved.