O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester | 1141487-92-4

• 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-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester
• 英文别名: 3-((2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)methyl)-4-phenyl-1,2,5-oxadiazole 2-oxide；(2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• CAS: 1141487-92-4
• 化学式: C₂₆H₁₈N₂O₈
• 分子量: 486.438
• InChiKey: HNJJFOAMCSHSLO-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  749.0±70.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester 、 乙酸酐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以43.5%的产率得到O5-acetyl-O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester
  参考文献：
  名称：

  Furoxan nitric oxide donor coupled chrysin derivatives: Synthesis and vasculoprotection

  摘要：

  A series of furoxan-based nitric oxide-releasing chrysin derivatives were synthesized. Pharmacological assays indicated that all chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-product formation. Some chrysin derivatives were also found to increase the glucose consumption of HepG2 cells. Furthermore, the compounds released a low amount of NO in the presence of L-cysteine (range from 0.20% to 1.89%). These hybrid furoxan-based NO donor chrysin derivatives offer a mutual prodrug 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.bmcl.2010.12.077
• 作为产物：
  描述：

  白杨素 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester
  参考文献：
  名称：

  Furoxan nitric oxide donor coupled chrysin derivatives: Synthesis and vasculoprotection

  摘要：

  A series of furoxan-based nitric oxide-releasing chrysin derivatives were synthesized. Pharmacological assays indicated that all chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-product formation. Some chrysin derivatives were also found to increase the glucose consumption of HepG2 cells. Furthermore, the compounds released a low amount of NO in the presence of L-cysteine (range from 0.20% to 1.89%). These hybrid furoxan-based NO donor chrysin derivatives offer a mutual prodrug 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.bmcl.2010.12.077

文献信息

• Furoxan nitric oxide donor coupled chrysin derivatives: Synthesis and vasculoprotection
  作者：Xiao-Qing Zou、Sheng-Ming Peng、Chang-Ping Hu、Li-Feng Tan、Han-Wu Deng、Yuan-Jian Li

  DOI：10.1016/j.bmcl.2010.12.077

  日期：2011.2

  A series of furoxan-based nitric oxide-releasing chrysin derivatives were synthesized. Pharmacological assays indicated that all chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-product formation. Some chrysin derivatives were also found to increase the glucose consumption of HepG2 cells. Furthermore, the compounds released a low amount of NO in the presence of L-cysteine (range from 0.20% to 1.89%). These hybrid furoxan-based NO donor chrysin derivatives offer a mutual prodrug design concept for the development of therapeutic or preventive agents for vascular complications due to diabetes. (C) 2010 Elsevier Ltd. All rights reserved.