2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸乙酯 | 1141487-91-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸乙酯
• 英文名称: O7-nitrooxyethyl chrysin
• 英文别名: 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)ethyl nitrate；2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyethyl nitrate
• CAS: 1141487-91-3
• 化学式: C₁₇H₁₃NO₇
• 分子量: 343.293
• InChiKey: NLJRSLKTBHDLMH-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  581.0±50.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸乙酯 、 乙酸酐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以28.6%的产率得到O5-acetyl-O7-nitrooxyethyl 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
• 作为产物：
  描述：

  7-(2-溴乙氧基)-5-羟基-2-苯基-4H-色烯-4-酮 在 silver nitrate 作用下， 以 乙腈 为溶剂， 生成 2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸乙酯
  参考文献：
  名称：

  Synthesis and promotion angiogenesis effect of chrysin derivatives coupled to NO donors

  摘要：

  Two types of new chrysin derivatives were prepared by coupling NO donors of alkyl nitrate and furazan derivatives and were fully characterized by H-1 NMR and other techniques. These compounds were tested in human umbilical vein endothelial cells (HUVECs-12) and all the compounds exhibited cell proliferation. Notable effects of promoting angiogenesis were observed for all the modified compounds using chick chorioallantoic membrane (CAM) assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.116

文献信息

• Synthesis and promotion angiogenesis effect of chrysin derivatives coupled to NO donors
  作者：Sheng-Ming Peng、Xiao-Qing Zou、Hua-Lan Ding、Yong-Lan Ding、Yuan-Bin Lin

  DOI：10.1016/j.bmcl.2008.12.116

  日期：2009.2

  Two types of new chrysin derivatives were prepared by coupling NO donors of alkyl nitrate and furazan derivatives and were fully characterized by H-1 NMR and other techniques. These compounds were tested in human umbilical vein endothelial cells (HUVECs-12) and all the compounds exhibited cell proliferation. Notable effects of promoting angiogenesis were observed for all the modified compounds using chick chorioallantoic membrane (CAM) assay. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.