(E)-4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide

• 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: (E)-4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide
• 英文别名: (E)-4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-N'-(pyridin-4-ylmethylene) benzohydrazide (12)；4-(5,6-dimethyl-1H-benzimidazol-2-yl)-N-[(E)-(2-hydroxy-5-methoxyphenyl)methylideneamino]benzamide
• 化学式: C₂₄H₂₂N₄O₃
• 分子量: 414.464
• InChiKey: PUHMFFITRCHBKS-DHRITJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  sodium hydroxy(4-(methoxycarbonyl)phenyl)methanesulfonate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 21.0h， 生成 (E)-4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide
  参考文献：
  名称：

  Benzimidazole derivatives protect against cytokine-induced apoptosis in pancreatic β-Cells

  摘要：

  Apoptotic cell death is the cause of the loss of insulin-producing beta-cells in all forms of diabetes mellitus. The identification of small molecules capable of protecting cytokine-induced apoptosis could form the basis of useful therapeutic interventions. Here in, we present the discovery and synthesis of new benzimidazole derivatives, capable of rescuing pancreatic beta-cells from cytokine-induced apoptosis. Three hydrazone derivatives of benzimidazole significantly increased the cellular ATP levels, reduced caspase-3 activity, reduced nitrite production and increased glucose-stimulated insulin secretion in the presence of proinflammatory cytokines. These findings suggest that these compounds may protect beta-cells from the harmful effects of cytokines and may serve as candidates for therapeutic intervention for diabetes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.022

文献信息

• Benzimidazole derivatives as new α-glucosidase inhibitors and in silico studies
  作者：Nik Khairunissa Nik Abdullah Zawawi、Muhammad Taha、Norizan Ahmat、Abdul Wadood、Nor Hadiani Ismail、Fazal Rahim、Syed Sikander Azam、Noraishah Abdullah

  DOI：10.1016/j.bioorg.2015.11.006

  日期：2016.2

  Newly synthesized benzimidazole hydrazone derivatives 1-26 were evaluated for their a-glucosidase inhibitory activity. Compounds 1-26 exhibited varying degrees of yeast a-glucosidase inhibitory activity with IC50 values between 8.40 +/- 0.76 and 179.71 +/- 1.11 mu M when compared with standard acarbose. In this assay, seven compounds that showed highest inhibitory effects than the rest of benzimidazole series were identified. All the synthesized compounds were characterized by different spectroscopic methods adequately. We further evaluated the interaction of the active compounds with enzyme with the help of docking studies. (C) 2015 Elsevier Inc. All rights reserved.
• Benzimidazole derivatives protect against cytokine-induced apoptosis in pancreatic β-Cells
  作者：Nik Khairunissa Nik Abdullah Zawawi、Sajid Ali Rajput、Muhammad Taha、Norizan Ahmat、Nor Hadiani Ismail、Noraishah Abdullah、Khalid Mohammed Khan、M. Iqbal Choudhary

  DOI：10.1016/j.bmcl.2015.08.022

  日期：2015.10

  Apoptotic cell death is the cause of the loss of insulin-producing beta-cells in all forms of diabetes mellitus. The identification of small molecules capable of protecting cytokine-induced apoptosis could form the basis of useful therapeutic interventions. Here in, we present the discovery and synthesis of new benzimidazole derivatives, capable of rescuing pancreatic beta-cells from cytokine-induced apoptosis. Three hydrazone derivatives of benzimidazole significantly increased the cellular ATP levels, reduced caspase-3 activity, reduced nitrite production and increased glucose-stimulated insulin secretion in the presence of proinflammatory cytokines. These findings suggest that these compounds may protect beta-cells from the harmful effects of cytokines and may serve as candidates for therapeutic intervention for diabetes. (C) 2015 Elsevier Ltd. All rights reserved.