1,3-bis((1-((3-oxo-3H-benzo[f]chromen-1-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 1,3-bis((1-((3-oxo-3H-benzo[f]chromen-1-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1,3-Bis[[1-[(3-oxobenzo[f]chromen-1-yl)methyl]triazol-4-yl]methyl]benzimidazol-2-one；1,3-bis[[1-[(3-oxobenzo[f]chromen-1-yl)methyl]triazol-4-yl]methyl]benzimidazol-2-one
• 化学式: C₄₁H₂₈N₈O₅
• 分子量: 712.724
• InChiKey: RBBFSMGVOSUGRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-羟基苯并咪唑 在 copper(ll) sulfate pentahydrate 、 四丁基溴化铵 、 sodium carbonate 、 potassium carbonate 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 1,3-bis((1-((3-oxo-3H-benzo[f]chromen-1-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies

  摘要：

  Nucleoside bases like uracil, pharmacophoric triazoles and benzimidazolones have been used during the present study to design molecular matrices for antitubercular activity, employing Click Chemistry. Click triazoles 4/7/10 have been obtained by the reaction of 4-(Azidomethyl)-2H-chromen-2-ones/quinolin-2(1H)-ones 3 and propargyl ethers 2/6/9 derived from theophylline/6-methyl uracil/2-benzimidazolone respectively. In addition to spectral data structures have been confirmed by single crystal X-ray diffraction studies in case of uracil bis alkyne (6) and theophylline mono triazole (4c). Theophylline linked mono triazoles, 4(a-d) and 6-methyl uracil linked bis triazoles, 7(a-e) have been found to inhibit Mycobacterium tuberculosis H37Rv with MIC values in the range 55.62-115.62 mu M. Benzimidazolone bis triazoles, 10(a-n) showed better activity with MIC in the range 2.33-18.34 mu M. Molecular modeling studies using Surflex-Dock algorithm supported our results.

  DOI：

  10.1016/j.bmc.2019.115054

文献信息

• A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies
  作者：Netravati Khanapurmath、Manohar V. Kulkarni、Shrinivas D. Joshi、G.N. Anil Kumar

  DOI：10.1016/j.bmc.2019.115054

  日期：2019.10

  Nucleoside bases like uracil, pharmacophoric triazoles and benzimidazolones have been used during the present study to design molecular matrices for antitubercular activity, employing Click Chemistry. Click triazoles 4/7/10 have been obtained by the reaction of 4-(Azidomethyl)-2H-chromen-2-ones/quinolin-2(1H)-ones 3 and propargyl ethers 2/6/9 derived from theophylline/6-methyl uracil/2-benzimidazolone respectively. In addition to spectral data structures have been confirmed by single crystal X-ray diffraction studies in case of uracil bis alkyne (6) and theophylline mono triazole (4c). Theophylline linked mono triazoles, 4(a-d) and 6-methyl uracil linked bis triazoles, 7(a-e) have been found to inhibit Mycobacterium tuberculosis H37Rv with MIC values in the range 55.62-115.62 mu M. Benzimidazolone bis triazoles, 10(a-n) showed better activity with MIC in the range 2.33-18.34 mu M. Molecular modeling studies using Surflex-Dock algorithm supported our results.