((2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromen-2-yl)methyl (E)-3-(3,4-dimethylphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromen-2-yl)methyl (E)-3-(3,4-dimethylphenyl)acrylate
• 英文别名: 11-O-(E)-3-(3,4-dimethylphenyl)acrylaldehyde bergenin；[(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl (E)-3-(3,4-dimethylphenyl)prop-2-enoate
• 化学式: C₂₅H₂₆O₁₀
• 分子量: 486.475
• InChiKey: OYRDOEBKRUKXDJ-BKDULIPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  岩白菜素 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 47.0h， 生成 ((2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromen-2-yl)methyl (E)-3-(3,4-dimethylphenyl)acrylate
  参考文献：
  名称：

  Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

  摘要：

  Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their anti-tumour activity both in vitro and in vivo. The most potent compound, 5c, arrested HepG2 cells (IC50 = 4.23 +/- 0.79 mu M) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bc1-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.053

文献信息

• Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids
  作者：Chengyuan Liang、Shaomeng Pei、Weihui Ju、Minyi Jia、Danni Tian、Yonghong Tang、Gennian Mao

  DOI：10.1016/j.ejmech.2017.03.053

  日期：2017.6

  Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their anti-tumour activity both in vitro and in vivo. The most potent compound, 5c, arrested HepG2 cells (IC50 = 4.23 +/- 0.79 mu M) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bc1-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies. (C) 2017 Elsevier Masson SAS. All rights reserved.