propanedioic acid mono[[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)-1,4-benzodioxin-2-yl]methyl] ethyl ester | 1174751-49-5

• 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: propanedioic acid mono[[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)-1,4-benzodioxin-2-yl]methyl] ethyl ester
• 英文别名: 1-O-ethyl 3-O-[[3-(4-hydroxy-3-methoxyphenyl)-6-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-2,3-dihydro-1,4-benzodioxin-2-yl]methyl] propanedioate
• CAS: 1174751-49-5
• 化学式: C₃₀H₂₈O₁₃
• 分子量: 596.545
• InChiKey: RBLQKXJCWRMIHN-QSUQFICRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  丙二酸单乙酯 、 silybin 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以35%的产率得到propanedioic acid mono[[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)-1,4-benzodioxin-2-yl]methyl] ethyl ester
  参考文献：
  名称：

  Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties

  摘要：

  A diverse series of C-23 esterified silybin derivatives (1a-n) were designed and synthesized. The antioxidative properties of these compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide anion radical scavenging, ferrous ion chelation, and inhibition of rat liver homogenate lipid peroxidation. Their protective effects on the prevention of hydrogen peroxide induced DNA damage were also investigated. Most of the synthesized compounds exhibited more effective antioxidant activities than silybin. The esterified silybin analogues displayed satisfactory performance especially on iron chelation and antiperoxidative activity. Compound 1n in particular exhibited remarkable antiperoxidative effect with an IC50 value of 0.2 +/- 0.1 mu M, which was stronger than that of quercetin (IC50 = 1.8 +/- 0.6 mu M). Compounds 1c, 1e, 1g, 1h and 1k displayed potent, dose-dependent protective properties against DNA cleavage. The results of the bioassays support the antioxidative and DNA protective effects of these synthesized silybin derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.023

文献信息

• Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties
  作者：Feng Wang、Kexin Huang、Leixiang Yang、Jingxu Gong、Qiaofeng Tao、Haibo Li、Yu Zhao、Su Zeng、Xiumei Wu、Joachim Stöckigt

  DOI：10.1016/j.bmc.2009.07.023

  日期：2009.9.1

  A diverse series of C-23 esterified silybin derivatives (1a-n) were designed and synthesized. The antioxidative properties of these compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide anion radical scavenging, ferrous ion chelation, and inhibition of rat liver homogenate lipid peroxidation. Their protective effects on the prevention of hydrogen peroxide induced DNA damage were also investigated. Most of the synthesized compounds exhibited more effective antioxidant activities than silybin. The esterified silybin analogues displayed satisfactory performance especially on iron chelation and antiperoxidative activity. Compound 1n in particular exhibited remarkable antiperoxidative effect with an IC50 value of 0.2 +/- 0.1 mu M, which was stronger than that of quercetin (IC50 = 1.8 +/- 0.6 mu M). Compounds 1c, 1e, 1g, 1h and 1k displayed potent, dose-dependent protective properties against DNA cleavage. The results of the bioassays support the antioxidative and DNA protective effects of these synthesized silybin derivatives. (C) 2009 Elsevier Ltd. All rights reserved.