4-nitro-N-(2-(5-nitro-1H-benzimidazol-2-yl)ethyl)benzamide | 1531631-27-2

• 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: 4-nitro-N-(2-(5-nitro-1H-benzimidazol-2-yl)ethyl)benzamide
• 英文别名: 4-Nitro-N-(2-(5-nitro-1H-benzimidazol-2-yl)ethyl)benzamide；4-nitro-N-[2-(6-nitro-1H-benzimidazol-2-yl)ethyl]benzamide
• CAS: 1531631-27-2
• 化学式: C₁₆H₁₃N₅O₅
• 分子量: 355.31
• InChiKey: PLWXLHNFUKWUMR-UHFFFAOYSA-N

物化性质

• 沸点：
  730.1±50.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基邻苯二胺 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 4-nitro-N-(2-(5-nitro-1H-benzimidazol-2-yl)ethyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and enzyme kinetics of novel benzimidazole and quinoxaline derivatives as methionine synthase inhibitors

  摘要：

  Methionine synthase catalyzes the transfer of a methyl group from 5-methyltetrahydrofolate to homocysteine, producing methionine and tetrahydrofolate. Benzimidazole and deazatetrahydrofolates derivatives have been shown to inhibit methionine synthase by competing with the substrate 5-methyltetrahydrofolate. In this study, a novel series of substituted benzimidazoles and quinoxalines were designed and assessed for inhibitory activity against purified rat liver methionine synthase using a radiometric enzyme assay. Compounds 3g, 3j, and 5c showed the highest activity against methionine synthase (IC50: 20 mu M, 18 mu M, 9 mu M, respectively). Kinetic analysis of these compounds using Lineweaver-Burk plots revealed characteristics of mixed inhibition for 3g and 5c; and uncompetitive inhibition for 3j. Docking study into a homology model of the rat methionine synthase gave insights into the molecular determinants of the activity of this class of compounds. The identification of these drug-like inhibitors could lead the design of the next generation modulators of methionine synthase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.052

文献信息

• Design, synthesis, and enzyme kinetics of novel benzimidazole and quinoxaline derivatives as methionine synthase inhibitors
  作者：Hosam Elshihawy、Mohamed A. Helal、Mohamed Said、Mohamed A. Hammad

  DOI：10.1016/j.bmc.2013.10.052

  日期：2014.1

  Methionine synthase catalyzes the transfer of a methyl group from 5-methyltetrahydrofolate to homocysteine, producing methionine and tetrahydrofolate. Benzimidazole and deazatetrahydrofolates derivatives have been shown to inhibit methionine synthase by competing with the substrate 5-methyltetrahydrofolate. In this study, a novel series of substituted benzimidazoles and quinoxalines were designed and assessed for inhibitory activity against purified rat liver methionine synthase using a radiometric enzyme assay. Compounds 3g, 3j, and 5c showed the highest activity against methionine synthase (IC50: 20 mu M, 18 mu M, 9 mu M, respectively). Kinetic analysis of these compounds using Lineweaver-Burk plots revealed characteristics of mixed inhibition for 3g and 5c; and uncompetitive inhibition for 3j. Docking study into a homology model of the rat methionine synthase gave insights into the molecular determinants of the activity of this class of compounds. The identification of these drug-like inhibitors could lead the design of the next generation modulators of methionine synthase. (C) 2013 Elsevier Ltd. All rights reserved.