3,5-dihydroxy-2-{2-hydroxymethyl-3-[3-methoxy-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)phenyl]-2,3-dihydrobenzo[1,4]dioxin-6-yl}-7-(2-oxo-2-pyrrolidin-1-yl-ethoxy)chromen-4-one | 1005737-32-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 3,5-dihydroxy-2-{2-hydroxymethyl-3-[3-methoxy-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)phenyl]-2,3-dihydrobenzo[1,4]dioxin-6-yl}-7-(2-oxo-2-pyrrolidin-1-yl-ethoxy)chromen-4-one
• CAS: 1005737-32-5
• 化学式: C₃₇H₃₈N₂O₁₂
• 分子量: 702.715
• InChiKey: XQXXUJNIOAASJR-JRYPVQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  51.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  177.67
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  (+/-)-silybin 、 (6CI,9CI)-1-(溴乙酰基)-吡咯烷 在 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以23%的产率得到3,5-dihydroxy-2-{2-hydroxymethyl-3-[3-methoxy-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)phenyl]-2,3-dihydrobenzo[1,4]dioxin-6-yl}-7-(2-oxo-2-pyrrolidin-1-yl-ethoxy)chromen-4-one
  参考文献：
  名称：

  Design, Synthesis, and Examination of Neuron Protective Properties of Alkenylated and Amidated Dehydro-Silybin Derivatives

  摘要：

  A series of C7-O- and C20-O-amidated 2,3-dehydrosilybin (DHS) derivatives ((+/-)-1a-f and (+/-)-2), as well its it set of alkenylated DHS analogues ((+/-)-4a-f), were designed and de novo synthesized. A diesteric derivative of DHS ((+/-)-3) and two C23 esterified DHS analogues ((+/-)-5a and (+/-)-5b) were also prepared for comparison. The cell viability of PC12 cells, Fe2+ chelation, lipid peroxiclation (LPO), freeradical scavenging, and xanthine oxidase inhibition models were utilized to evaluate their antioxidative and neuron protective properties. The study revealed that the diether at C7-OH and C20-OH as well as the monoether at C7-OH, which possess aliphatic substituted acetamides, demonstrated more potent LPO inhibition and Fe2+ chelation compared to DHS and quercetin. Conversely, the diallyl ether at C7-OH and C20-OH wits more potent in protection of PCl2 cells against H2O2-induced injury than DHS and quercetin. Overall, the more lipophilic alkenylated DHS analogues were better performing neuroprotective agents than the acetamidated derivatives. The results in this study would be beneficial for optimizing the therapeutic potential of lignoflavonoids, especially in neurodegenerative disorders such as Alzheimer's and Parkinson's disease.

  DOI：

  10.1021/jm900735p