2,5-bis(6-cyanoindol-2-yl)pyridine | 1428230-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,5-bis(6-cyanoindol-2-yl)pyridine
• 英文别名: 2-[6-(6-cyano-1H-indol-2-yl)pyridin-3-yl]-1H-indole-6-carbonitrile
• CAS: 1428230-61-8
• 化学式: C₂₃H₁₃N₅
• 分子量: 359.39
• InChiKey: ZRVMZOBFCLNGJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(6-cyanoindol-2-yl)pyridine 、 二甲胺 在 盐酸 作用下， 以 乙醇 、 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以74%的产率得到2,5-bis[6-(N,N-dimethylamidino)indol-2-yl]pyridine hydrochloric acid salt
  参考文献：
  名称：

  Synthesis and structure-activity relationship of novel bisindole amidines active against MDR Gram-positive and Gram-negative bacteria

  摘要：

  A series of novel diamidines with N-substituents on an amidine N-atom were synthesized and evaluated for their cytotoxicity and in vitro antibacterial activity against a range of Gram-positive and Gram-negative bacterial strains. Based on structure-activity relationship, N-substituents with a branched chain and a shorter carbon chain on the amidine N-atom exhibited more promising activity against Gram-negative and MDR-Gram-positive bacteria: compounds 5c and Si were the most powerful candidate compounds. Compound 5c showed greater efficacy than levofloxacin against most drug resistant Gram-positive bacteria and exhibited broad-spectrum antibacterial activity against Gram-negative bacteria, with MIC values in the range of 2-16 mu g/mL. Slightly more potent antibacterial activity against Klebsiella pneumoniae, Acinetobacter calcoaceticus, Enterobacter cloacae, and Proteus mirabilis was observed for 5i in comparison with 5c. Compound 5i also showed remarkable antibacterial activity against NDM-1-producing Gram-negative bacteria, with MIC values in the range of 2-4 mu g/mL, and was superior to the reference drugs meropenem and levofloxacin. Effective antibacterial activity of 5i was also shown in vivo in a mouse model of Staphylococcus aureus MRSA strain, with an ED(50)values of 2.62 mg/kg. (C) 2018 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2018.03.031
• 作为产物：
  描述：

  2-溴-5-碘吡啶 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.5h， 生成 2,5-bis(6-cyanoindol-2-yl)pyridine
  参考文献：
  名称：

  [EN] ANTIFUNGAL COMPOUNDS
  [FR] COMPOSÉS ANTIFONGIQUES

  摘要：

  公开号：

  WO2013052263A3

文献信息

• [EN] ANTIMICROBIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIMICROBIENS
  申请人：MICROBIOTIX INC

  公开号：WO2013040526A1

  公开（公告）日：2013-03-21

  The invention provides antimicrobial organic compounds and compositions thereof that kill or inhibit growth of cells of one or more microbial pathogens.

  这项发明提供了抗微生物有机化合物及其组合物，可杀灭或抑制一种或多种微生物病原体的细胞生长。
• Synthesis and structure-activity relationship of novel bisindole amidines active against MDR Gram-positive and Gram-negative bacteria
  作者：Yonghua Liu、Xinxin Hu、Yanbin Wu、Weixing Zhang、Xiaofang Chen、Xuefu You、Laixing Hu

  DOI：10.1016/j.ejmech.2018.03.031

  日期：2018.4

  A series of novel diamidines with N-substituents on an amidine N-atom were synthesized and evaluated for their cytotoxicity and in vitro antibacterial activity against a range of Gram-positive and Gram-negative bacterial strains. Based on structure-activity relationship, N-substituents with a branched chain and a shorter carbon chain on the amidine N-atom exhibited more promising activity against Gram-negative and MDR-Gram-positive bacteria: compounds 5c and Si were the most powerful candidate compounds. Compound 5c showed greater efficacy than levofloxacin against most drug resistant Gram-positive bacteria and exhibited broad-spectrum antibacterial activity against Gram-negative bacteria, with MIC values in the range of 2-16 mu g/mL. Slightly more potent antibacterial activity against Klebsiella pneumoniae, Acinetobacter calcoaceticus, Enterobacter cloacae, and Proteus mirabilis was observed for 5i in comparison with 5c. Compound 5i also showed remarkable antibacterial activity against NDM-1-producing Gram-negative bacteria, with MIC values in the range of 2-4 mu g/mL, and was superior to the reference drugs meropenem and levofloxacin. Effective antibacterial activity of 5i was also shown in vivo in a mouse model of Staphylococcus aureus MRSA strain, with an ED(50)values of 2.62 mg/kg. (C) 2018 Published by Elsevier Masson SAS.
• [EN] ANTIFUNGAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIFONGIQUES
  申请人：MICROBIOTIX INC

  公开号：WO2013052263A3

  公开（公告）日：2013-06-20