2-(1,1-di(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol 1,3-diacetate | 1333853-92-1

• 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: 2-(1,1-di(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol 1,3-diacetate
• 英文别名: [2-(Acetyloxymethyl)-3,3-bis(3,4,5-trimethoxyphenyl)prop-2-enyl] acetate
• CAS: 1333853-92-1
• 化学式: C₂₆H₃₂O₁₀
• 分子量: 504.534
• InChiKey: CCSYVICBLUNJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(1,1-di(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol 1,3-diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以60%的产率得到2-(1,1-di(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol
  参考文献：
  名称：

  Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds

  摘要：

  A series of diversely substituted biarylolefins based on carbohydrate and dihydroxyethylene scaffolds were synthesized and evaluated for antiproliferative activity against a panel of human tumor cell lines. Among the thirty-five yet unknown biarylolefins prepared, six displayed potent antiproliferative activities with IC50 values in the micromolar and submicromolar range. As a new type of antiproliferative agent, the most potent compound 26 showed an IC50 value of 70 nM against SK-OV3 cell line (ovarian cancer). All the synthesized compounds exhibited a poor or modest tubulin polymerization inhibitory activity suggesting another mode of action for these compounds. Molecular docking simulations to the colchicine binding site of tubulin of representative compounds have been used to explain the lack of activity as inhibitors of tubulin polymerization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.021
• 作为产物：
  描述：

  1,3-二乙酰氧基丙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 三(2-呋喃基)膦 、 potassium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-(1-bromo-1-(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol 1,3-diacetate 、 2-(1,1-di(3,4,5-trimethoxyphenyl)methylene)propan-1,3-diol 1,3-diacetate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds

  摘要：

  A series of diversely substituted biarylolefins based on carbohydrate and dihydroxyethylene scaffolds were synthesized and evaluated for antiproliferative activity against a panel of human tumor cell lines. Among the thirty-five yet unknown biarylolefins prepared, six displayed potent antiproliferative activities with IC50 values in the micromolar and submicromolar range. As a new type of antiproliferative agent, the most potent compound 26 showed an IC50 value of 70 nM against SK-OV3 cell line (ovarian cancer). All the synthesized compounds exhibited a poor or modest tubulin polymerization inhibitory activity suggesting another mode of action for these compounds. Molecular docking simulations to the colchicine binding site of tubulin of representative compounds have been used to explain the lack of activity as inhibitors of tubulin polymerization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.021

文献信息

• Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds
  作者：Alexandre Novoa、Nadia Pellegrini-Moïse、Stéphane Bourg、Sylviane Thoret、Joëlle Dubois、Geneviève Aubert、Thierry Cresteil、Yves Chapleur

  DOI：10.1016/j.ejmech.2011.05.021

  日期：2011.9

  A series of diversely substituted biarylolefins based on carbohydrate and dihydroxyethylene scaffolds were synthesized and evaluated for antiproliferative activity against a panel of human tumor cell lines. Among the thirty-five yet unknown biarylolefins prepared, six displayed potent antiproliferative activities with IC50 values in the micromolar and submicromolar range. As a new type of antiproliferative agent, the most potent compound 26 showed an IC50 value of 70 nM against SK-OV3 cell line (ovarian cancer). All the synthesized compounds exhibited a poor or modest tubulin polymerization inhibitory activity suggesting another mode of action for these compounds. Molecular docking simulations to the colchicine binding site of tubulin of representative compounds have been used to explain the lack of activity as inhibitors of tubulin polymerization. (C) 2011 Elsevier Masson SAS. All rights reserved.