(E)-3-[4-(dimethylamino)phenyl]-N-tosylacrylamide | 1332498-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-[4-(dimethylamino)phenyl]-N-tosylacrylamide
• 英文别名: (E)-3-[4-(dimethylamino)phenyl]-N-(4-methylphenyl)sulfonylprop-2-enamide
• CAS: 1332498-91-5
• 化学式: C₁₈H₂₀N₂O₃S
• 分子量: 344.434
• InChiKey: CCMGGDMGKDRMHX-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 哌啶 、 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (E)-3-[4-(dimethylamino)phenyl]-N-tosylacrylamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents

  摘要：

  A series of novel cinnamic acyl sulfonamide derivatives (9a-16e) have been designed and synthesized and their biological activities were also evaluated as potential tubulin polymerization inhibitors. Among all the compounds, 10c showed the most potent growth inhibitory activity against B16-F10 cancer cell line in vitro, with an IC50 value of 0.8 mu g/mL. Docking simulation was performed to insert compound 10c into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 10c with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.088

文献信息

• Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis
  作者：Zheng-Yang Gu、Yang Wu、Xiaoguang Bao、Ji-Bao Xia、Feng Jin

  DOI：10.1055/a-1401-4486

  日期：2021.9

  alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

  已经开发了原子和步长经济的分子间多组分钯催化烯烃与一氧化碳和有机叠氮化物的CH酰胺化反应，用于合成烯基酰胺。该反应在烯烃底物上没有邻位基团的情况下有效地进行。无毒的二氮是唯一的副产物。计算研究和对照实验表明，该反应是通过串联钯催化的意外机制发生的。
• Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents
  作者：Yin Luo、Ke-Ming Qiu、Xiang Lu、Kai Liu、Jie Fu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.06.088

  日期：2011.8

  A series of novel cinnamic acyl sulfonamide derivatives (9a-16e) have been designed and synthesized and their biological activities were also evaluated as potential tubulin polymerization inhibitors. Among all the compounds, 10c showed the most potent growth inhibitory activity against B16-F10 cancer cell line in vitro, with an IC50 value of 0.8 mu g/mL. Docking simulation was performed to insert compound 10c into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 10c with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.