5-bromo-2-(4-butoxyphenyl)-1H-benzo[d]imidazole

• 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: 5-bromo-2-(4-butoxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 6-bromo-2-(4-butoxyphenyl)-1H-benzimidazole
• 化学式: C₁₇H₁₇BrN₂O
• 分子量: 345.239
• InChiKey: LLRCXNPQZPBECD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴邻苯二胺 、 4-丁氧基苯甲醛 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以51%的产率得到5-bromo-2-(4-butoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Syntheses, in vitro evaluation and molecular docking studies of 5-bromo-2-aryl benzimidazoles as α-glucosidase inhibitors

  摘要：

  Based on the previous reports on alpha-glucosidase inhibitory activity of benzimidazole class, we intend to evaluate further this class as potential inhibitors of alpha-glucosidase enzyme. Thus, in the current study synthesis of 5-bromo-2-aryl benzimidazole derivatives 1-25 was carried out. All the synthetic compounds were characterized by different spectroscopic techniques EIMS, HRMS, H-1-NMR, and C-13-NMR. Molecular docking was also performed on the selected compounds 1, 4, 7, and 17 having varying substitution pattern in order to understand the molecular interaction of molecules with the active site of the enzyme. All compounds were evaluated for their in vitro alpha-glucosidase inhibitory activities. Twenty-three compounds out of twenty-five showed excellent to moderate activity in the range of IC50 = 12.4-103.2 mu M. Inhibitory results were compared with the standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Compounds 1 (IC50 = 37.82 +/- 0.08 mu M), 9 (IC50 = 37.76 +/- 0.05 mu M), 12 (IC50 = 24.96 +/- 0.09 mu M), 16 (IC50 = 21.15 +/- 0.08 mu M) and 17 (IC50 = 8.34 +/- 0.02 mu M) showed excellent inhibition as compared to standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Especially, 17 (IC50 = 8.34 +/- 0.02 mu M) was found to be five-fold more active than the standard.

  DOI：

  10.1007/s00044-016-1614-y

文献信息

• Syntheses, in vitro evaluation and molecular docking studies of 5-bromo-2-aryl benzimidazoles as α-glucosidase inhibitors
  作者：Tanzila Arshad、Khalid Mohammed Khan、Najma Rasool、Uzma Salar、Shafqat Hussain、Tehreem Tahir、Mohammed Ashraf、Abdul Wadood、Muhammad Riaz、Shahnaz Perveen、Muhammad Taha、Nor Hadiani Ismail

  DOI：10.1007/s00044-016-1614-y

  日期：2016.9

  Based on the previous reports on alpha-glucosidase inhibitory activity of benzimidazole class, we intend to evaluate further this class as potential inhibitors of alpha-glucosidase enzyme. Thus, in the current study synthesis of 5-bromo-2-aryl benzimidazole derivatives 1-25 was carried out. All the synthetic compounds were characterized by different spectroscopic techniques EIMS, HRMS, H-1-NMR, and C-13-NMR. Molecular docking was also performed on the selected compounds 1, 4, 7, and 17 having varying substitution pattern in order to understand the molecular interaction of molecules with the active site of the enzyme. All compounds were evaluated for their in vitro alpha-glucosidase inhibitory activities. Twenty-three compounds out of twenty-five showed excellent to moderate activity in the range of IC50 = 12.4-103.2 mu M. Inhibitory results were compared with the standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Compounds 1 (IC50 = 37.82 +/- 0.08 mu M), 9 (IC50 = 37.76 +/- 0.05 mu M), 12 (IC50 = 24.96 +/- 0.09 mu M), 16 (IC50 = 21.15 +/- 0.08 mu M) and 17 (IC50 = 8.34 +/- 0.02 mu M) showed excellent inhibition as compared to standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Especially, 17 (IC50 = 8.34 +/- 0.02 mu M) was found to be five-fold more active than the standard.