N-pentyl-2-(chloromethyl)benzimidazole

• 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: N-pentyl-2-(chloromethyl)benzimidazole
• 英文别名: 2-(Chloromethyl)-1-pentylbenzimidazole
• 化学式: C₁₃H₁₇ClN₂
• 分子量: 236.744
• InChiKey: MQAKMPPVYCQEKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-pentyl-2-(chloromethyl)benzimidazole 、 环丙沙星 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以56.6%的产率得到1-cyclopropyl-6-fluoro-4-oxo-7-(4-((1-pentyl-1H-benzimidazol-2-yl)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents

  摘要：

  A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 mu M concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.052
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-pentyl-2-(chloromethyl)benzimidazole
  参考文献：
  名称：

  独特的 13-（苯并咪唑基甲基）小檗碱作为有前途的广谱抗菌剂的新发现

  摘要：

  对小檗碱和苯并咪唑进行了新的杂交，以生产 13-(苯并咪唑基甲基)小檗碱 (BMB) 作为潜在的广谱抗菌剂，有望应对畜牧业中的多重耐药细菌感染。一些新制备的杂种对受试菌株表现出明显的抗菌作用。特别是，发现 13-((1-辛基-苯并咪唑基)甲基)小檗碱6f (OBMB- 6f ) 是最有前途的化合物，它不仅具有强活性 (MIC = 0.25–2 μg/mL) 和低细胞毒性，而且还具有快速杀菌能力和对金黄色葡萄球菌和大肠杆菌产生抗药性的低倾向即使在 26 个连续段落之后。此外，OBMB- 6f显示出在低温和高温下防止细菌生物膜形成的能力。机理探索表明，OBMB- 6f可以显着分解细菌膜，显着促进细胞内ROS的产生，并有效地嵌入DNA中。这些结果为 BMB 在畜牧业中对抗多重耐药细菌感染提供了深刻的见解。

  DOI：

  10.1021/acs.jafc.2c03849

文献信息

• 喹诺酮苯并咪唑类化合物及其制备方法和应 用
  申请人：西南大学

  公开号：CN104974138B

  公开（公告）日：2018-01-05

  本发明公开了喹诺酮苯并咪唑类化合物及其制备方法和应用，结构如通式(I)所示，该化合物具有抗微生物活性，对革兰氏阳性菌、革兰氏阴性菌和真菌都有一定的抑制活性，用于制备抗细菌和/或抗真菌药物，还可以与药学上的辅料组合制成单方或复方制剂。并且本发明公开的化合物所涉及的制备原料商业化程度高、便宜易得，制备路线短、方法简便，生产成本低，为临床抗微生物治疗提供更多高效、安全的候选药物。通用分子式中R1、R2、R3、R4、R5、R6、R7和X如权利要求书所定义。
• Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents
  作者：Ling Zhang、Dinesh Addla、Jeyakkumar Ponmani、Ao Wang、Dan Xie、Ya-Nan Wang、Shao-Lin Zhang、Rong-Xia Geng、Gui-Xin Cai、Shuo Li、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2016.01.052

  日期：2016.3

  A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 mu M concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities. (C) 2016 Elsevier Masson SAS. All rights reserved.
• A New Discovery of Unique 13-(Benzimidazolylmethyl)berberines as Promising Broad-Spectrum Antibacterial Agents
  作者：Hang Sun、Zhen-Zhen Li、Ponmani Jeyakkumar、Zhong-Lin Zang、Bo Fang、Cheng-He Zhou

  DOI：10.1021/acs.jafc.2c03849

  日期：2022.10.5

  produce 13-(benzimidazolylmethyl)berberines (BMB) as potentially broad-spectrum antibacterial agents with the hope of confronting multidrug-resistant bacterial infections in the livestock industry. Some of the newly prepared hybrids showed obvious antibacterial effects against tested strains. Particularly, 13-((1-octyl-benzimidazolyl)methyl)berberine 6f (OBMB-6f) was found to be the most promising compound

  对小檗碱和苯并咪唑进行了新的杂交，以生产 13-(苯并咪唑基甲基)小檗碱 (BMB) 作为潜在的广谱抗菌剂，有望应对畜牧业中的多重耐药细菌感染。一些新制备的杂种对受试菌株表现出明显的抗菌作用。特别是，发现 13-((1-辛基-苯并咪唑基)甲基)小檗碱6f (OBMB- 6f ) 是最有前途的化合物，它不仅具有强活性 (MIC = 0.25–2 μg/mL) 和低细胞毒性，而且还具有快速杀菌能力和对金黄色葡萄球菌和大肠杆菌产生抗药性的低倾向即使在 26 个连续段落之后。此外，OBMB- 6f显示出在低温和高温下防止细菌生物膜形成的能力。机理探索表明，OBMB- 6f可以显着分解细菌膜，显着促进细胞内ROS的产生，并有效地嵌入DNA中。这些结果为 BMB 在畜牧业中对抗多重耐药细菌感染提供了深刻的见解。