4-((4-(hydroxyamino)-4-oxobutoxy)carbonyl)benzo[c][1,2,5]oxadiazole 1-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-((4-(hydroxyamino)-4-oxobutoxy)carbonyl)benzo[c][1,2,5]oxadiazole 1-oxide
• 英文别名: [4-(Hydroxyamino)-4-oxobutyl] 1-oxido-2,1,3-benzoxadiazol-1-ium-4-carboxylate；[4-(hydroxyamino)-4-oxobutyl] 1-oxido-2,1,3-benzoxadiazol-1-ium-4-carboxylate
• 化学式: C₁₁H₁₁N₃O₆
• 分子量: 281.225
• InChiKey: AWSBDNSOALCBQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-Azido-3-nitro-benzoesaeure 在 Jones reagent 、 盐酸羟胺 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 26.5h， 生成 4-((4-(hydroxyamino)-4-oxobutoxy)carbonyl)benzo[c][1,2,5]oxadiazole 1-oxide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel histone deacetylases inhibitors with nitric oxide releasing activity

  摘要：

  A novel series of histone deacetylases inhibitors (HDACIs) containing benzofuroxan pharmacophore as nitric oxide (NO) donor were designed based on the combination principle and 'multifunctional drugs' theory. As a novel study on embedding NO donor into the structure of HDACIs, all designed hybrid compounds, especially 19d and 24d, displayed remarkable HDACs inhibitory activity and outstanding antiproliferative activity on tumor cells. Besides, they could produce high levels of NO in HCT-116 cells; furthermore, their antiproliferative activity on HCT-116 cells could be diminished by pretreatment with hemoglobin, as the NO scavenger, in a dose-dependent manner. All in all, our designed compounds displayed great inhibitory activities and might offer a prospective avenue to discover novel anti-cancer drugs. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.015

文献信息

• Synthesis and biological evaluation of novel histone deacetylases inhibitors with nitric oxide releasing activity
  作者：Wenwen Duan、Jinning Hou、Xiaojing Chu、Xiaoqian Li、Jian Zhang、Jin Li、Wenfang Xu、Yingjie Zhang

  DOI：10.1016/j.bmc.2015.06.015

  日期：2015.8

  A novel series of histone deacetylases inhibitors (HDACIs) containing benzofuroxan pharmacophore as nitric oxide (NO) donor were designed based on the combination principle and 'multifunctional drugs' theory. As a novel study on embedding NO donor into the structure of HDACIs, all designed hybrid compounds, especially 19d and 24d, displayed remarkable HDACs inhibitory activity and outstanding antiproliferative activity on tumor cells. Besides, they could produce high levels of NO in HCT-116 cells; furthermore, their antiproliferative activity on HCT-116 cells could be diminished by pretreatment with hemoglobin, as the NO scavenger, in a dose-dependent manner. All in all, our designed compounds displayed great inhibitory activities and might offer a prospective avenue to discover novel anti-cancer drugs. (C) 2015 Elsevier Ltd. All rights reserved.