N-[(3-bromophenyl)methylideneamino]naphthalene-2-carboxamide | 340228-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(3-bromophenyl)methylideneamino]naphthalene-2-carboxamide
• CAS: 340228-63-9
• 化学式: C₁₈H₁₃BrN₂O
• 分子量: 353.218
• InChiKey: DUVJWYNTQLNDIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(3-bromophenyl)methylideneamino]naphthalene-2-carboxamide 在 potassium iodide 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 生成 2-(3-bromophenyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  10.2174/157017861466617081115

  摘要：

  DOI：

  10.2174/157017861466617081115
• 作为产物：
  描述：

  2-萘甲酸乙酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 N-[(3-bromophenyl)methylideneamino]naphthalene-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin-A4 as novel antitubulin agents

  摘要：

  A total of 20 novel 1,3,4-oxadiazoline analogs (6a-6t) of combretastatin A-4 with naphthalene ring were designed, synthesized, and evaluated for biological activities as potential tubulin polymerization inhibitors. Among these compounds, 6n showed the most potent antiproliferative activities against multiple cancer cell lines and retained the microtubule disrupting effects. Docking simulation was performed to insert compound 6n into the crystal structure of tubulin to determine the probable binding model. These results indicated oxadiazoline compounds bearing the naphthyl moiety are promising tubulin inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.057

文献信息

• 10.2174/157017861466617081115
  作者：Khan, P. Rasvan、Durgaprasad、Reddy, S. Gopal、Reddy, G. Raveendra、Hussein, Ibnelwaleed A.、Reddy, B.V. Subba

  DOI：10.2174/157017861466617081115

  日期：——
• Design, synthesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin-A4 as novel antitubulin agents
  作者：Yang Hu、Xiang Lu、Ke Chen、Ru Yan、Qing-Shan Li、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.11.057

  日期：2012.1

  A total of 20 novel 1,3,4-oxadiazoline analogs (6a-6t) of combretastatin A-4 with naphthalene ring were designed, synthesized, and evaluated for biological activities as potential tubulin polymerization inhibitors. Among these compounds, 6n showed the most potent antiproliferative activities against multiple cancer cell lines and retained the microtubule disrupting effects. Docking simulation was performed to insert compound 6n into the crystal structure of tubulin to determine the probable binding model. These results indicated oxadiazoline compounds bearing the naphthyl moiety are promising tubulin inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.