6-(1H-benzo[d]imidazol-2-yl)-4-(4-nitrophenyl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)nicotinonitrile | 1575824-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(1H-benzo[d]imidazol-2-yl)-4-(4-nitrophenyl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)nicotinonitrile
• CAS: 1575824-03-1
• 化学式: C₂₈H₁₇N₇O₅S
• 分子量: 563.553
• InChiKey: UEAPGDGBBROFSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  41.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  171.95
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 在 ammonium acetate 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 38.0h， 生成 6-(1H-benzo[d]imidazol-2-yl)-4-(4-nitrophenyl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)nicotinonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs

  摘要：

  A series of 6-(1H-benzo[d]imidazol-2-yl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-yl)-4-(aryl)nicotinonitriles 5a-l were synthesized and characterized by IR, H-1 NMR, C-13 NMR, and mass spectrometry techniques. These novel compounds 5a-l were screened for their in vitro antimicrobial activity against different bacterial and fungal strains and in vitro cytotoxicity study (HeLa cell line) using MTT colorimetric assay. The results demonstrated that compounds 5c, 5e, and 5i-k exhibited excellent antibacterial activity, while compounds 5d, 5i, and 5k were found to be the most potent antifungal agents. From the standpoint of SAR studies, it was observed that the presence of electron donating groups remarkably enhanced the antimicrobial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5c-e and 5i-k was accompanied by low cytotoxicity.

  DOI：

  10.1007/s00044-014-0971-7