2-cyclohexyl-6-(4-fluorophenoxy)-5-(pent-4-enamido)-1H-benzo[d]imidazole | 1448875-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyclohexyl-6-(4-fluorophenoxy)-5-(pent-4-enamido)-1H-benzo[d]imidazole
• 英文别名: N-[2-cyclohexyl-6-(4-fluorophenoxy)-1H-benzimidazol-5-yl]pent-4-enamide；N-[2-cyclohexyl-6-(4-fluorophenoxy)-3H-benzimidazol-5-yl]pent-4-enamide
• CAS: 1448875-90-8
• 化学式: C₂₄H₂₆FN₃O₂
• 分子量: 407.488
• InChiKey: GEXIJBSNXVHPQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二硝基-5-氟苯胺 在 吡啶 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 33.0h， 生成 2-cyclohexyl-6-(4-fluorophenoxy)-5-(pent-4-enamido)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Design, synthesis and evaluation of novel 2,5,6-trisubstituted benzimidazoles targeting FtsZ as antitubercular agents

  摘要：

  Filamenting temperature-sensitive protein Z (FtsZ), an essential cell division protein, is a promising target for the drug discovery of new-generation antibacterial agents against various bacterial pathogens. As a part of SAR studies on benzimidazoles, we have synthesized a library of 376 novel 2,5,6-trisubstituted benzimidazoles, bearing ether or thioether linkage at the 6-position. In a preliminary HTP screening against Mtb H37Rv, 108 compounds were identified as hits at a cut off concentration of 5 mu g/mL. Among those hits, 10 compounds exhibited MIC values in the range of 0.63-12.5 mu g/mL. Light scattering assay and TEM analysis with the most potent compound 5a clearly indicate that its molecular target is Mtb-FtsZ. Also, the K-d of 5a with Mtb-FtsZ was determined to be 1.32 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.035

文献信息

• [EN] BENZIMIDAZOLES AND USES THEREOF<br/>[FR] BENZIMIDAZOLES ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2013116823A1

  公开（公告）日：2013-08-08

  The present invention relates to novel 2,5,6-benzimidazole derivatives of formula I and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis or Mycobacteriumavium complex by administering to the patient a 2,5,6- benzimidazole derivative or a pharmaceutically acceptable salt thereof.

  本发明涉及公式I的新颖2,5,6-苯并咪唑衍生物及其药学上可接受的盐。发明的另一个方面涉及通过向患有结核分枝杆菌或分枝杆菌复合物感染的患者施用2,5,6-苯并咪唑衍生物或其药学上可接受的盐来治疗患者的方法。