O7-[(nitrooxyl)ethoxycarbonyl] methyl chrysin | 1227681-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: O7-[(nitrooxyl)ethoxycarbonyl] methyl chrysin
• 英文别名: 2-(nitrooxy)ethyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetate；2-nitrooxyethyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• CAS: 1227681-44-8
• 化学式: C₁₉H₁₅NO₉
• 分子量: 401.329
• InChiKey: FTCDFUOMOQLAII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  O7-[(bromoethoxyl)carbonyl]methyl chrysin 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以44.9%的产率得到O7-[(nitrooxyl)ethoxycarbonyl] methyl chrysin
  参考文献：
  名称：

  Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin

  摘要：

  Vascular complications are major causes of disability and death in patients with diabetes mellitus. It is often characterized by endothelial dysfunction. Studies have shown that either the loss of nitric oxide bioactivity or the decreased biosynthesis of NO is a central mechanism in endothelial dysfunction. As such, the delivery of exogenous NO is an attractive therapeutic option that has been used to slow the progress of diabetic vascular complications. In this paper, a novel group of hybrid nitric oxide-releasing chrysin derivatives was synthesized. The results indicated that all these chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-products formation. And some of them were even found to increase the glucose consumption of HepG2 cells. Furthermore, all compounds released NO upon incubation with phosphate buffer at pH 7.4. These hybrid ester NO donor pro-drugs offer a potential drug design concept for the development of therapeutic or preventive agents for vascular complications due to diabetes. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.056

文献信息

• Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin
  作者：Xiao-Qing Zou、Sheng-Ming Peng、Chang-Ping Hu、Li-Feng Tan、Qiong Yuan、Han-Wu Deng、Yuan-Jian Li

  DOI：10.1016/j.bmc.2010.03.056

  日期：2010.5

  Vascular complications are major causes of disability and death in patients with diabetes mellitus. It is often characterized by endothelial dysfunction. Studies have shown that either the loss of nitric oxide bioactivity or the decreased biosynthesis of NO is a central mechanism in endothelial dysfunction. As such, the delivery of exogenous NO is an attractive therapeutic option that has been used to slow the progress of diabetic vascular complications. In this paper, a novel group of hybrid nitric oxide-releasing chrysin derivatives was synthesized. The results indicated that all these chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-products formation. And some of them were even found to increase the glucose consumption of HepG2 cells. Furthermore, all compounds released NO upon incubation with phosphate buffer at pH 7.4. These hybrid ester NO donor pro-drugs offer a potential drug design concept for the development of therapeutic or preventive agents for vascular complications due to diabetes. (c) 2010 Elsevier Ltd. All rights reserved.