2-(2-(5-((pyridin-4-ylamino)methyl)furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetohydrazide

• 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: 2-(2-(5-((pyridin-4-ylamino)methyl)furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetohydrazide
• 英文别名: 2-[2-[5-[(Pyridin-4-ylamino)methyl]furan-2-yl]benzimidazol-1-yl]acetohydrazide；2-[2-[5-[(pyridin-4-ylamino)methyl]furan-2-yl]benzimidazol-1-yl]acetohydrazide
• 化学式: C₁₉H₁₈N₆O₂
• 分子量: 362.391
• InChiKey: GRGQKPUSPPAJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  麦穗宁 在 盐酸 、 hydrazine hydrate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 2-(2-(5-((pyridin-4-ylamino)methyl)furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Part I. Synthesis, biological evaluation and docking studies of new 2-furylbenzimidazoles as antiangiogenic agents

  摘要：

  2-(2-Furyl)-1H-benzimidazoles 3-11 were synthesized and tested for their in vitro VEGF inhibition in MCF-7 cancer cell line. Compound 5a was more potent than Tamoxifen, and compounds 3b, 5a, 5c, 6b, 7a and 10 showed promising potency. Furthermore, compounds (6b, 7a and 10) showed remarkable selective inhibition of COX-2 enzyme close to that of Celecoxcib. Additionally, docking studies were performed using AutoDock 4.2 into the VEGFR2 kinase. Significant correlation exists between the biological activity (IC50 and %VEGF inhibition) against MCF-7 cell line and the molecular docking results (K-i and Delta G(b)) with correlation coefficients (R-2) of 0.5513 and 0.4623 respectively. Accordingly, most of the synthesized 2-(2-furyl)-1H-benzimidazoles showed strong antiangiogenic activity against VEGFR2 kinase. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.063

文献信息

• Part I. Synthesis, biological evaluation and docking studies of new 2-furylbenzimidazoles as antiangiogenic agents
  作者：Ahmed Temirak、Yasser M. Shaker、Fatma A.F. Ragab、Mamdouh M. Ali、Hamed I. Ali、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2014.01.063

  日期：2014.11

  2-(2-Furyl)-1H-benzimidazoles 3-11 were synthesized and tested for their in vitro VEGF inhibition in MCF-7 cancer cell line. Compound 5a was more potent than Tamoxifen, and compounds 3b, 5a, 5c, 6b, 7a and 10 showed promising potency. Furthermore, compounds (6b, 7a and 10) showed remarkable selective inhibition of COX-2 enzyme close to that of Celecoxcib. Additionally, docking studies were performed using AutoDock 4.2 into the VEGFR2 kinase. Significant correlation exists between the biological activity (IC50 and %VEGF inhibition) against MCF-7 cell line and the molecular docking results (K-i and Delta G(b)) with correlation coefficients (R-2) of 0.5513 and 0.4623 respectively. Accordingly, most of the synthesized 2-(2-furyl)-1H-benzimidazoles showed strong antiangiogenic activity against VEGFR2 kinase. (c) 2014 Elsevier Masson SAS. All rights reserved.