2-benzyl-1-phenyl-1H-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: 2-benzyl-1-phenyl-1H-benzimidazole
• 英文别名: 1-phenyl-2-phenylmethylbenzimidazole；2-Benzyl-1-phenylbenzimidazole
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: BWBYHJJTLBESHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-benzyl-1-phenyl-1H-benzimidazole 、 gold(I) chloride 以 乙醚 为溶剂， 反应 1.0h， 以25%的产率得到VZM043
  参考文献：
  名称：

  Gold complexes with benzimidazole derivatives: synthesis, characterization and biological studies

  摘要：

  Synthesis, characterization, DFT studies and biological assays of new gold(I) and gold(III) complexes of benzimidazole are reported. Molecular and structural characterizations of the compounds were based on elemental (C, H and N) and thermal (TG-DTA) analyses, and FT-IR and UV-Visible spectroscopic measurements. The structures of complexes were proposed based DFT calculations. The benzimidazole compounds (Lig1 and Lig2) and the gold complexes were tested against three Leishmania species related to cutaneous manifestations of leishmaniasis. The free benzimidazole compounds showed no leishmanicidal activity. On the other hand, the gold(I and III) complexes have shown to possess significant activity against Leishmania in both stages of parasite, and the gold(III) complex with Lig2 exhibited expressive leishmanicidal activity with IC50 values below 5.7 mu M. Also, the gold complexes showed high leishmania selectivity. The gold(I) complex with Lig1, for example, is almost 50 times more toxic for the parasite than for macrophages. Besides the leishmanicidal activity, all complexes exhibited toxic effect against SK-Mel 103 and Balb/c 3T3, cancer cells.

  DOI：

  10.1007/s10534-014-9703-1
• 作为产物：
  描述：

  2,2-dibromostyrene 、 邻氨基二苯胺 在 三乙烯二胺 作用下， 以 1-methyl-2-pyrrolidinone 为溶剂， 以55%的产率得到2-benzyl-1-phenyl-1H-benzimidazole
  参考文献：
  名称：

  由1，1-二溴乙烯合成苯并咪唑

  摘要：

  描述了一种温和而有效的方法，用于由1,1-二溴乙烯和邻二氨基苯制备取代的苯并咪唑。该反应以DABCO为碱，NMP为溶剂。在2-芳基-1，1-二溴乙烯和邻-二氨基苯上的各种取代是可容忍的。该新方法在温和的碱性条件下进行，可能为现有苯并咪唑制剂提供补充途径。

  DOI：

  10.1016/j.tetlet.2008.10.030

文献信息

• Methods of treating or preventing interstitial cystitis
  申请人：Eli Lilly and Company

  公开号：US06025379A1

  公开（公告）日：2000-02-15

  This invention provides methods for the treatment or prevention of interstitial cystitis or urethral syndrome in a mammal which comprise administering to a mammal in need thereof an effective amount of a substituted benzimidazole, or a pharmaceutically acceptable salt or solvate thereof.

  这项发明提供了治疗或预防哺乳动物间质性膀胱炎或尿道综合征的方法，包括向需要的哺乳动物施用有效量的取代苯并咪唑或其药用可接受盐或溶剂。
• Methods for treating a physiological disorder associated with
  申请人：Eli Lilly and Company

  公开号：US05552426A1

  公开（公告）日：1996-09-03

  This invention provides substituted benzimidazoles which are useful in treating or preventing conditions associated with .beta.-amyloid peptide. Some such conditions associated with .beta.-amyloid peptide include Alzheimer's Disease, Down's Syndrome and amyloidosis of the Dutch type.

  这项发明提供了一种替代苯并咪唑，可用于治疗或预防与β-淀粉样肽相关的疾病。与β-淀粉样肽相关的一些疾病包括阿尔茨海默病、唐氏综合征和荷兰型淀粉样变性。
• Non-peptidyl tachykinin receptor antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0694535A1

  公开（公告）日：1996-01-31

  This invention provides novel substituted benzimidazoles of formula II which are useful as tachykinin receptor antagonists. This invention also provides methods for treating a condition associated with an excess of tachykinin which comprises administering to a mammal in need thereof one of a series of substituted benzimidazoles. This invention further provides pharmaceutical formulations comprising one or more of the substituted benzimidazoles of the present invention in association with pharmaceutical carriers, diluents, or excipients. A and Ra-Re are as defined in the description.

  这项发明提供了一种新颖的公式II的取代苯并咪唑，它们可用作快速激肽受体拮抗剂。这项发明还提供了治疗与快速激肽过剩有关的疾病的方法，包括向需要的哺乳动物中给予一系列取代苯并咪唑中的一种。这项发明还提供了包含本发明中一种或多种取代苯并咪唑与药用载体、稀释剂或赋形剂相关联的药物配方。A和Ra-Re如描述中所定义。
• US6030992
  申请人：——

  公开号：——

  公开（公告）日：——
• US5552426A
  申请人：——

  公开号：US5552426A

  公开（公告）日：1996-09-03