ethyl 3,4,5-trimethyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate | 1179588-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3,4,5-trimethyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate
• 英文别名: Ethyl 3,4,5-trimethyl-1-[(3,4,5-trimethoxyphenyl)methyl]pyrrole-2-carboxylate
• CAS: 1179588-15-8
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: ROSFLHLHMSMLNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,5-trimethyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate 、 二乙二醇 在 potassium hydroxide 作用下， 反应 3.0h， 以34%的产率得到2-(2-hydroxyethoxy)ethyl 3,4,5-trimethyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  New Arylthioindoles and Related Bioisosteres at the Sulfur Bridging Group. 4. Synthesis, Tubulin Polymerization, Cell Growth Inhibition, and Molecular Modeling Studies

  摘要：

  New arylthioindoles along with the corresponding ketone and methylene compounds were potent tubulin assembly inhibitors. As growth inhibitors of MCF-7 cells, sulfur derivatives were superior or sometimes equivalent to the ketones, while methylene derivatives were substantially less effective. Esters 24, 27-29, 36, 39, and 41 showed similar to 50% of inhibition oil human HeLa and HCT116/chr3 cells at 0.5 mu M, and these compounds inhibited the growth of HEK, M 14, and U937 cells with IC50'S ill the 78220 nM range. While murine macrophage J744.1 cell growth was significantly less affected (20% at higher concentrations), four other nontransformed cell lines remained sensitive to these esters. The effect of drug treatment oil cell morphology was examined by time-lapse microscopy. In a protocol set up to evaluate toxicity on the Saccharomyces cerevisiae BY4741 wild type strain, compounds 24 and 54 strongly reduced cell growth, and 29, 36, and 39 also showed significant inhibition.

  DOI：

  10.1021/jm900016t
• 作为产物：
  描述：

  3,4,5-三甲基吡咯-2-甲基乙酯 、 3,4,5-三甲氧基苄氯 在 四丁基硫酸氢铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以45%的产率得到ethyl 3,4,5-trimethyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  New Arylthioindoles and Related Bioisosteres at the Sulfur Bridging Group. 4. Synthesis, Tubulin Polymerization, Cell Growth Inhibition, and Molecular Modeling Studies

  摘要：

  New arylthioindoles along with the corresponding ketone and methylene compounds were potent tubulin assembly inhibitors. As growth inhibitors of MCF-7 cells, sulfur derivatives were superior or sometimes equivalent to the ketones, while methylene derivatives were substantially less effective. Esters 24, 27-29, 36, 39, and 41 showed similar to 50% of inhibition oil human HeLa and HCT116/chr3 cells at 0.5 mu M, and these compounds inhibited the growth of HEK, M 14, and U937 cells with IC50'S ill the 78220 nM range. While murine macrophage J744.1 cell growth was significantly less affected (20% at higher concentrations), four other nontransformed cell lines remained sensitive to these esters. The effect of drug treatment oil cell morphology was examined by time-lapse microscopy. In a protocol set up to evaluate toxicity on the Saccharomyces cerevisiae BY4741 wild type strain, compounds 24 and 54 strongly reduced cell growth, and 29, 36, and 39 also showed significant inhibition.

  DOI：

  10.1021/jm900016t

文献信息

• New Arylthioindoles and Related Bioisosteres at the Sulfur Bridging Group. 4. Synthesis, Tubulin Polymerization, Cell Growth Inhibition, and Molecular Modeling Studies
  作者：Giuseppe La Regina、Taradas Sarkar、Ruoli Bai、Michael C. Edler、Roberto Saletti、Antonio Coluccia、Francesco Piscitelli、Lara Minelli、Valerio Gatti、Carmela Mazzoccoli、Vanessa Palermo、Cristina Mazzoni、Claudio Falcone、Anna Ivana Scovassi、Vincenzo Giansanti、Pietro Campiglia、Amalia Porta、Bruno Maresca、Ernest Hamel、Andrea Brancale、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm900016t

  日期：2009.12.10

  New arylthioindoles along with the corresponding ketone and methylene compounds were potent tubulin assembly inhibitors. As growth inhibitors of MCF-7 cells, sulfur derivatives were superior or sometimes equivalent to the ketones, while methylene derivatives were substantially less effective. Esters 24, 27-29, 36, 39, and 41 showed similar to 50% of inhibition oil human HeLa and HCT116/chr3 cells at 0.5 mu M, and these compounds inhibited the growth of HEK, M 14, and U937 cells with IC50'S ill the 78220 nM range. While murine macrophage J744.1 cell growth was significantly less affected (20% at higher concentrations), four other nontransformed cell lines remained sensitive to these esters. The effect of drug treatment oil cell morphology was examined by time-lapse microscopy. In a protocol set up to evaluate toxicity on the Saccharomyces cerevisiae BY4741 wild type strain, compounds 24 and 54 strongly reduced cell growth, and 29, 36, and 39 also showed significant inhibition.