1-(2-bromoethyl)-1H-benzo[d]imidazole | 90326-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-bromoethyl)-1H-benzo[d]imidazole
• 英文别名: 3-Bromoethylbenzimidazole；1-(2-bromoethyl)benzimidazole
• CAS: 90326-34-4
• 化学式: C₉H₉BrN₂
• mdl: MFCD09816604
• 分子量: 225.088
• InChiKey: KPDMESZOWPPZMA-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  329.7±44.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(2-bromoethyl)-1H-benzo[d]imidazole 、 6-(4-吗啉)-1H-嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 以52.2%的产率得到4-(9-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-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
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 生成 1-(2-bromoethyl)-1H-benzo[d]imidazole
  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

• 10.1016/j.bioorg.2024.107425
  作者：Iqbal, Shazia、Sebhaoui, Jihad、Ashraf, Sajda、Ozcan, Mehmet、Kim, Woonghee、Belmen, Burcu、Yeşilyurt, Güldeniz、Hanashalshahaby, Essam、Zhang, Cheng、Uhlen, Mathias、Boren, Jan、Turkez, Hasan、Mardinoglu, Adil

  DOI：10.1016/j.bioorg.2024.107425

  日期：——

  (NAFLD) comprises a broad range of liver disease including hepatocellular carcinoma (HCC) with is no FDA-approved drug. Liver pyruvate kinase (PKL) is a major regulator of metabolic flux and ATP generation in liver presenting a potential target for the treatment of NAFLD. Based on our recent finding of JNK-5A's effectiveness in inhibiting PKLR expression through a drug repositioning pipeline, this

  非酒精性脂肪性肝病 (NAFLD) 包括多种肝脏疾病，包括肝细胞癌 (HCC)，且尚未获得 FDA 批准的药物。肝脏丙酮酸激酶 (PKL) 是肝脏代谢通量和 ATP 生成的主要调节因子，是治疗 NAFLD 的潜在靶点。基于我们最近发现 JNK-5A 通过药物重新定位管道有效抑制 PKLR 表达，本研究旨在进一步提高其疗效。我们在分子对接研究的指导下合成了一系列具有针对性修饰的 JNK-5A 类似物。评估了这些化合物对人 HepG2 细胞系中 PKL 表达、细胞活力、三酰甘油 (TAG) 水平以及脂肪变性相关蛋白表达的活性。随后，评估了这些化合物在降低 TAG 水平和毒性方面的功效。化合物 (SET-151) 和 (SET-152) 被证明在降低 HepG2 中 TAG 水平方面最有效（11.51 ± 0.90 % 和 10.77 ± 0.67 %），并且毒性较低（61.60 ± 5.00 %
• 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.