4-((5-fluoro-3-oxobenzo[d][1,2]selenazol-2(3H)-yl)methyl)-N-hydroxybenzamide

• 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: 4-((5-fluoro-3-oxobenzo[d][1,2]selenazol-2(3H)-yl)methyl)-N-hydroxybenzamide
• 英文别名: 4-[(5-fluoro-3-oxo-1,2-benzoselenazol-2-yl)methyl]-N-hydroxybenzamide
• 化学式: C₁₅H₁₁FN₂O₃Se
• 分子量: 365.222
• InChiKey: AYAGAKOUIMAONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(chloroselenyl)-5-fluorobenzoyl chloride 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 9.0h， 生成 4-((5-fluoro-3-oxobenzo[d][1,2]selenazol-2(3H)-yl)methyl)-N-hydroxybenzamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of histone deacetylase inhibitors possessing glutathione peroxidase-like and antioxidant activities against Alzheimer’s disease

  摘要：

  A series of hybrids containing the pharmacophores of the histone deacetylase (HDAC) inhibitor, SAHA, and the antioxidant ebselen were designed and synthesized as multi-target-directed ligands against Alzheimer's disease. An in vitro assay indicated that some of these molecules exhibit potent HDAC inhibitory activity and ebselen-related pharmacological effects. Specifically, the optimal compound 7f was found to be a potent HDAC inhibitor (IC50 = 0.037 mu M), possessing rapid hydrogen peroxide scavenging activity and glutathione peroxidase-like activity (nu(0) = 150.0 mu M min(-1)) and good free oxygen radical absorbance capacity (value of ORAC: 2.2). Furthermore, compound 7f showed significant protective effects against damage induced by H2O2 and the ability to prevent ROS accumulation in PC12 cells.

  DOI：

  10.1016/j.bmc.2018.10.022

文献信息

• Design, synthesis, and biological evaluation of histone deacetylase inhibitors possessing glutathione peroxidase-like and antioxidant activities against Alzheimer’s disease
  作者：Jinhui Hu、Baijiao An、Tingting Pan、Zhengcunxiao Li、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2018.10.022

  日期：2018.11

  A series of hybrids containing the pharmacophores of the histone deacetylase (HDAC) inhibitor, SAHA, and the antioxidant ebselen were designed and synthesized as multi-target-directed ligands against Alzheimer's disease. An in vitro assay indicated that some of these molecules exhibit potent HDAC inhibitory activity and ebselen-related pharmacological effects. Specifically, the optimal compound 7f was found to be a potent HDAC inhibitor (IC50 = 0.037 mu M), possessing rapid hydrogen peroxide scavenging activity and glutathione peroxidase-like activity (nu(0) = 150.0 mu M min(-1)) and good free oxygen radical absorbance capacity (value of ORAC: 2.2). Furthermore, compound 7f showed significant protective effects against damage induced by H2O2 and the ability to prevent ROS accumulation in PC12 cells.