methyl 2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)-4-methylbenzoate | 1235837-71-4

• 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: methyl 2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)-4-methylbenzoate
• 英文别名: Methyl 2-[2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetyl]oxy-4-methylbenzoate
• CAS: 1235837-71-4
• 化学式: C₂₆H₂₀O₈
• 分子量: 460.44
• InChiKey: HSSDIDYYUZJCRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)乙酸 、 4-甲基水杨酸甲酯 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以70%的产率得到methyl 2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)-4-methylbenzoate
  参考文献：
  名称：

  Synthesis, biological evaluation of chrysin derivatives as potential immunosuppressive agents

  摘要：

  A series of novel chrysin derivatives was firstly synthesized and evaluated on their immunosuppressive activity in the search for potential immunosuppressive agents. Among them, compounds 5c displayed the most potent immunosuppressive inhibitory activity with IC50 of 0.78 mu M, which was comparable to that of cyclosporin A (IC50 = 0.06 mu M). The preliminary mechanism of compound 5c inhibition effects was also detected by flow cytometry (FCM), and the compound exerted immunosuppressive activity via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Furthermore, the estimated LD50 (in mg/kg) in vivo of compound 5c is 738.2, which indicated that compound 5c was low toxic. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.034

文献信息

• Synthesis, biological evaluation of chrysin derivatives as potential immunosuppressive agents
  作者：Peng-Cheng Lv、Tian-Tian Cai、Yong Qian、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.10.034

  日期：2011.1

  A series of novel chrysin derivatives was firstly synthesized and evaluated on their immunosuppressive activity in the search for potential immunosuppressive agents. Among them, compounds 5c displayed the most potent immunosuppressive inhibitory activity with IC50 of 0.78 mu M, which was comparable to that of cyclosporin A (IC50 = 0.06 mu M). The preliminary mechanism of compound 5c inhibition effects was also detected by flow cytometry (FCM), and the compound exerted immunosuppressive activity via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Furthermore, the estimated LD50 (in mg/kg) in vivo of compound 5c is 738.2, which indicated that compound 5c was low toxic. (C) 2010 Elsevier Masson SAS. All rights reserved.