2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile | 869767-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile
• 英文别名: 2-[4-(4-cyanophenyl)phenyl]-3H-benzimidazole-5-carbonitrile
• CAS: 869767-76-0
• 化学式: C₂₁H₁₂N₄
• 分子量: 320.353
• InChiKey: MUYJLZVZUADHOE-UHFFFAOYSA-N

物化性质

• 熔点：
  311-312 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  616.0±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile 在 羟胺 作用下， 以 二甲基亚砜 为溶剂， 生成 2-[4'-(N-hydroxyamidino)biphenyl-4-yl]-1H-benzimidazole-5-N-hydroxyamidine
  参考文献：
  名称：

  [EN] DICATIONIC TRIARYL ANALOGS AS ANTI-PROTOZOAN AGENTS
  [FR] ANALOGUES TRIARYL DICATIONIQUES UTILISES EN TANT QU'AGENTS ANTIPROTOZOAIRES

  摘要：

  新颖的二正离子、杂环三芳基化合物在治疗微生物感染方面很有用，例如Trypanosoma brucei rhodesiense感染和Plasmodium falciparum感染。因此，这些化合物在治疗第二阶段的人类非洲锥虫病中很有用。含有这些化合物的药物配方可用于治疗微生物感染的方法。

  公开号：

  WO2005040132A1
• 作为产物：
  描述：

  4-溴苯腈 在 四(三苯基膦)钯 sodium carbonate 、 sodium hydrogensulfite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile
  参考文献：
  名称：

  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

  摘要：

  A series of near-linear biphenyl benzimidazole diamidines 5a-h were synthesized from their respective diamidoximes (4a-h), through the bis-O-acetoxyamidoxime, followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. Compounds 4a-h were obtained in three steps, starting with the Suzuki coupling reaction of the appropriate haloarylcarbonitriles la-g or 4-bromo-2-fluorobenzaldehyde with 4-formylphenylboronic acid or 4-cyanophenylboronic acid to form the anticipated 4-formylbiphenyl carbonitrile analogues 2a-h. Subsequent condensation of the formyl derivatives 2a-h with 3,4-diaminobenzonitrile in the presence of sodium bisulfite or 1,4-benzoquinone gave the desired dinitriles 3a-h, the precursors for 4a-h. All the diamidines showed strong DNA affinities, as judged by high Delta T-m values with poly(dA.dT)(2). The compounds were quite active in vitro versus Trypanosoma brucei rhodesiense, giving IC50 values ranging from 3 to 37 nM. These compounds were even more active versus Plasmodium falciparum, exhibiting IC50 values ranging from 0.5 to 23 nM. The compounds showed moderate to good activity in vivo in the STIB900 model for acute African trypanosomiasis. The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.024