N-(5-(4-bromophenyl)-1H-pyrazol-3-yl)cinnamamide

• 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-(5-(4-bromophenyl)-1H-pyrazol-3-yl)cinnamamide
• 英文别名: N-[5-(4-bromophenyl)-1H-pyrazol-3-yl]-3-phenylprop-2-enamide
• 化学式: C₁₈H₁₄BrN₃O
• 分子量: 368.233
• InChiKey: KKTVIBAOELMNLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苯甲酰乙腈 在 甲烷磺酸 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(5-(4-bromophenyl)-1H-pyrazol-3-yl)cinnamamide
  参考文献：
  名称：

  Synthesis, biological evaluation and 3D-QSAR studies of novel 5-phenyl-1H-pyrazol cinnamamide derivatives as novel antitubulin agents

  摘要：

  A series of novel 5-phenyl-1H-pyrazol derivatives (5a-5x) containing cinnamamide moiety were synthesized and their biological activities as potential tubulin polymerization inhibitors were evaluated. Among them, compound 5j exhibited the most potent inhibitory activity with an IC50 value of 1.02 mu M for tubulin, which was superior to that of Colchicine (IC50 = 1.34 mu M). Docking simulation was performed to insert compound 5j into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent tubulin inhibitory activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.018

文献信息

• Synthesis, biological evaluation and 3D-QSAR studies of novel 5-phenyl-1H-pyrazol cinnamamide derivatives as novel antitubulin agents
  作者：Shu-Fu Wang、Yong Yin、Ya-Liang Zhang、Shan-Wei Mi、Meng-Yue Zhao、Peng-Cheng Lv、Bao-Zhong Wang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2015.02.018

  日期：2015.3

  A series of novel 5-phenyl-1H-pyrazol derivatives (5a-5x) containing cinnamamide moiety were synthesized and their biological activities as potential tubulin polymerization inhibitors were evaluated. Among them, compound 5j exhibited the most potent inhibitory activity with an IC50 value of 1.02 mu M for tubulin, which was superior to that of Colchicine (IC50 = 1.34 mu M). Docking simulation was performed to insert compound 5j into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent tubulin inhibitory activity. (C) 2015 Elsevier Masson SAS. All rights reserved.