6-(N,N-diethylamino)-2-phenyl-5-(4-methylbenzamido)-1H-benzo[d]imidazole | 1434143-15-3

• 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: 6-(N,N-diethylamino)-2-phenyl-5-(4-methylbenzamido)-1H-benzo[d]imidazole
• 英文别名: N-[6-(diethylamino)-2-phenyl-3H-benzimidazol-5-yl]-4-methylbenzamide
• CAS: 1434143-15-3
• 化学式: C₂₅H₂₆N₄O
• 分子量: 398.508
• InChiKey: LMLFLDUTVNHBLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二硝基-5-氟苯胺 在 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 6-(N,N-diethylamino)-2-phenyl-5-(4-methylbenzamido)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Benzimidazole-based antibacterial agents against Francisella tularensis

  摘要：

  Francisella tularensis is a highly virulent pathogenic bacterium. In order to identify novel potential antibacterial agents against F. tularensis, libraries of trisubstituted benzimidazoles were screened against F. tularensis LVS strain. In a preliminary screening assay, remarkably, 23 of 2,5,6- and 2,5,7-trisubstituted benzimidazoles showed excellent activity exhibiting greater than 90% growth inhibition at 1 mu g/mL. Among those hits, 21 compounds showed MIC90 values in the range of 0.35-48.6 mu g/mL after accurate MIC determination. In ex vivo efficacy assays, four of these compounds exhibited 2-3 log reduction in colony forming units (CFU) per mL at concentrations of 10 and 50 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.059

文献信息

• BENZIMIDAZOLES AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：Ojima Iwao

  公开号：US20100256203A1

  公开（公告）日：2010-10-07

  The present invention relates to novel benzimidazole derivatives and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis or Francisella tulerensis by administering to the patient a benzimidazole derivative or a pharmaceutically acceptable salt thereof.

  本发明涉及新型苯并咪唑衍生物及其药学上可接受的盐。本发明的另一方面涉及通过向患者给予苯并咪唑衍生物或其药学上可接受的盐来治疗Mycobacterium tuberculosis或Francisella tulerensis感染的患者的方法。
• US8232410B2
  申请人：——

  公开号：US8232410B2

  公开（公告）日：2012-07-31
• [EN] BENZIMIDAZOLES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] BENZIMIDAZOLES ET COMPOSITIONS PHARMACEUTIQUES DE CEUX-CI
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2008130669A1

  公开（公告）日：2008-10-30

  [EN] The present invention relates to novel benzimidazole derivatives and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating a patient infected by Mycobacterium tuberculosis or Francisella tulerensis by administering to the patient a benzimidazole derivative or a pharmaceutically acceptable salt thereof.
  [FR] L'invention concerne de nouveaux dérivés du benzimidazole et des sels pharmaceutiquement acceptables de ceux-ci. Un autre aspect de l'invention concerne des procédés de traitement d'un patient infecté par Mycobacterium tuberculosis ou Francisella tulerensis par l'administration au patient d'un dérivé du benzimidazole ou d'un sel pharmaceutiquement acceptable de celui-ci.
• [EN] 5-CARBONYLAMINO-/(SULFONAMIDO-) SUBSTITUTED BENZ IMIDAZOLES AND USE THEREOF TREATMENT OF TUBERCULOSIS<br/>[FR] BENZ IMIDAZOLES SUBSTITUÉS 5-CARBONYLAMINO-/ (SULFONAMIDO-) ET UTILISATION DE CELUI-CI ET LE TRAITEMENT DE LA TUBERCULOSE
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2013142326A1

  公开（公告）日：2013-09-26

  The present invention discloses novel 5-/6- or 5-/7- substituded benzimidazoles and pharmaceutically acceptable salts thereof. Another aspect of the invention relates to their use in treating a patient infected by Mycobacterium tuberculosis or Francisella tularensis.
• Benzimidazole-based antibacterial agents against Francisella tularensis
  作者：Kunal Kumar、Divya Awasthi、Seung-Yub Lee、Jason E. Cummings、Susan E. Knudson、Richard A. Slayden、Iwao Ojima

  DOI：10.1016/j.bmc.2013.02.059

  日期：2013.6

  Francisella tularensis is a highly virulent pathogenic bacterium. In order to identify novel potential antibacterial agents against F. tularensis, libraries of trisubstituted benzimidazoles were screened against F. tularensis LVS strain. In a preliminary screening assay, remarkably, 23 of 2,5,6- and 2,5,7-trisubstituted benzimidazoles showed excellent activity exhibiting greater than 90% growth inhibition at 1 mu g/mL. Among those hits, 21 compounds showed MIC90 values in the range of 0.35-48.6 mu g/mL after accurate MIC determination. In ex vivo efficacy assays, four of these compounds exhibited 2-3 log reduction in colony forming units (CFU) per mL at concentrations of 10 and 50 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.