O5-acetyl-O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester | 1245649-42-6

• 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: O5-acetyl-O7-chrysinacetic acid (4-phenyl-1,2,5-oxadiazole-2-oxide-3-yl)methyl ester
• 英文别名: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(5-acetyloxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• CAS: 1245649-42-6
• 化学式: C₂₈H₂₀N₂O₉
• 分子量: 528.475
• InChiKey: YBBFTRDITKQNEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 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 、 丙酮 为溶剂， 生成 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

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.