N-4-toluenesulfonyl-(E)-3-(4-bromophenyl)prop-2-enamide | 1332498-81-3

• 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: N-4-toluenesulfonyl-(E)-3-(4-bromophenyl)prop-2-enamide
• 英文别名: (E)-3-(4-bromophenyl)-N-tosylacrylamide；(E)-3-(4-bromophenyl)-N-(4-methylphenyl)sulfonylprop-2-enamide
• CAS: 1332498-81-3
• 化学式: C₁₆H₁₄BrNO₃S
• 分子量: 380.262
• InChiKey: POZWYAGBFLOBOO-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 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 N-4-toluenesulfonyl-(E)-3-(4-bromophenyl)prop-2-enamide
  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

• Cu-Catalyzed Conversion of Propargyl Acetates to <i>E</i>-α,β-Unsaturated Amides via Ketenimine Formation with Sulfonyl Azides
  作者：Yalla Kiran Kumar、Gadi Ranjith Kumar、Maddi Sridhar Reddy

  DOI：10.1021/jo402570t

  日期：2014.1.17

  β-unsaturated N-tosylamides via N-sulfonyl ketenimine formation followed by a probable 1,3-OAc migration ([3,3]-sigmatropic rearrangement). The reaction is very general, allowing all kinds of substitution, including alkyl, aryl (electron-donating, -withdrawing, and -neutral), heteroaryl, and vinyl groups, on the C-terminal of acrylamide. Also, the method affords the products at ambient temperature

  在CuI催化剂存在下，易得的炔丙基乙酸酯与磺酰叠氮化物之间的反应通过N-磺酰基酮亚胺的形成产生反式-α，β-不饱和N-甲苯磺酰胺，然后可能发生1,3-OAc迁移（[3,3]- σ重排）。该反应非常普遍，允许在丙烯酰胺的C端进行各种取代，包括烷基，芳基（供电子，吸电子和-中性），杂芳基和乙烯基。同样，该方法在环境温度下以中等至良好的产率提供了优异的非对映选择性。
• 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.