4-(9-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl)-9H-purin-6-yl)morpholine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-(9-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl)-9H-purin-6-yl)morpholine
• 英文别名: 4-[9-[(1-Ethylbenzimidazol-2-yl)methyl]purin-6-yl]morpholine；4-[9-[(1-ethylbenzimidazol-2-yl)methyl]purin-6-yl]morpholine
• 化学式: C₁₉H₂₁N₇O
• 分子量: 363.422
• InChiKey: RJZWKTWNRFFGCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-N-乙基苯-1,2-二胺 在 盐酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 4-(9-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl)-9H-purin-6-yl)morpholine
  参考文献：
  名称：

  Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove

  摘要：

  A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus ( MIC = 4 mu g/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c-DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.046

文献信息

• Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove
  作者：Ya-Nan Wang、Rammohan R. Yadav Bheemanaboina、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2018.03.046

  日期：2018.5

  A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus ( MIC = 4 mu g/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c-DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity. (C) 2018 Elsevier Ltd. All rights reserved.