<(3,4,5-Trimethoxy-benzoyl)-acetessigsaeure>-ethylester | 194021-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(3,4,5-Trimethoxy-benzoyl)-acetessigsaeure>-ethylester
• 英文别名: 3-oxo-2-(3,4,5-trimethoxy-benzoyl)-butyric acid ethyl ester；α-Trimethylgalloyl-acetessigsaeure-aethylester；3-Oxo-2-(3,4,5-trimethoxy-benzoyl)-buttersaeure-aethylester；α-(3.4.5-Trimethoxy-benzoyl)-acetessigsaeure-aethylester；Ethyl 3-oxo-2-(3,4,5-trimethoxybenzoyl)butanoate；ethyl 3-oxo-2-(3,4,5-trimethoxybenzoyl)butanoate
• CAS: 194021-21-1
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: XMDHUXBICPXDJY-UHFFFAOYSA-N

物化性质

• 沸点：
  423.0±40.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  <(3,4,5-Trimethoxy-benzoyl)-acetessigsaeure>-ethylester 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙醚 为溶剂， 生成 ethyl 2-bromo-3-oxo-3-(3,4,5-trimethoxyphenyl)propanoate
  参考文献：
  名称：

  Imidazolone–amide bridges and their effects on tubulin polymerization in cis-locked vinylogous combretastatin-A4 analogues: Synthesis and biological evaluation

  摘要：

  A series of novel combretastatin-A4 analogues in which the cis-olefinic bridge is replaced by an imidazolone-amide were synthesized, and their cytotoxicity and tubulin-polymerization inhibitory activities were evaluated. These compounds appear to be potential tubulin-polymerization inhibitors. Compounds 10, 9b and 9c, bearing 3'-NH2-4'-OCH3, 4'-CH3 and 3'-CH3-substituted 1-phenyl B-ring, confer optimal bioactivity. The binding modes of these compounds to tubulin were obtained by molecular docking, which can explain the compounds' structure-activity relationship. The studies presented here provide a new structural type for the development of novel antitumor agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.068
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 乙醚 、 五氯化磷 作用下， 生成 <(3,4,5-Trimethoxy-benzoyl)-acetessigsaeure>-ethylester
  参考文献：
  名称：

  Perkin; Weizmann, Journal of the Chemical Society, 1906, vol. 89, p. 1655

  摘要：

  DOI：

文献信息

• Bradley; Robinson, Journal of the Chemical Society, 1928, p. 1551
  作者：Bradley、Robinson

  DOI：——

  日期：——
• Analogs of Windaus' Anhydride. Synthesis of 2,3-Dimethoxy-9-benzoyl-aminobenzosuber-5-ene-5,6-dicarboxylic Anhydride^1,2
  作者：John Koo

  DOI：10.1021/ja01099a063

  日期：1953.2
• Hebky et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1291,1292
  作者：Hebky et al.

  DOI：——

  日期：——
• Perkin; Weizmann, Journal of the Chemical Society, 1906, vol. 89, p. 1655
  作者：Perkin、Weizmann

  DOI：——

  日期：——
• Imidazolone–amide bridges and their effects on tubulin polymerization in cis-locked vinylogous combretastatin-A4 analogues: Synthesis and biological evaluation
  作者：Yao-Wu Li、Jia Liu、Na Liu、Duo Shi、Xiao-Tian Zhou、Jia-Guo Lv、Ju Zhu、Can-Hui Zheng、You-Jun Zhou

  DOI：10.1016/j.bmc.2011.03.068

  日期：2011.6

  A series of novel combretastatin-A4 analogues in which the cis-olefinic bridge is replaced by an imidazolone-amide were synthesized, and their cytotoxicity and tubulin-polymerization inhibitory activities were evaluated. These compounds appear to be potential tubulin-polymerization inhibitors. Compounds 10, 9b and 9c, bearing 3'-NH2-4'-OCH3, 4'-CH3 and 3'-CH3-substituted 1-phenyl B-ring, confer optimal bioactivity. The binding modes of these compounds to tubulin were obtained by molecular docking, which can explain the compounds' structure-activity relationship. The studies presented here provide a new structural type for the development of novel antitumor agents. (C) 2011 Elsevier Ltd. All rights reserved.