2-(4-bromophenyl)-N-(4-fluorophenylsulfonyl)acetamide | 1342254-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-bromophenyl)-N-(4-fluorophenylsulfonyl)acetamide
• 英文别名: 2-(4-bromophenyl)-N-(4-fluorophenyl)sulfonylacetamide
• CAS: 1342254-00-5
• 化学式: C₁₄H₁₁BrFNO₃S
• 分子量: 372.215
• InChiKey: ONQVMCPUHNXZRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟苯磺酰胺 、 对溴苯乙酸 在 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 12.0h， 以83%的产率得到2-(4-bromophenyl)-N-(4-fluorophenylsulfonyl)acetamide
  参考文献：
  名称：

  Metronidazole acid acyl sulfonamide: A novel class of anticancer agents and potential EGFR tyrosine kinase inhibitors

  摘要：

  A series of novel metronidazole derivatives were recently reported as potent anticancer agents targeting EGFR and HER-2 by our group [Qian, Y.; Zhang, H. J.; Zhang, H.; Xu, C.; Zhao, J.; Zhu, H. L Bioorg. Med. Chem. 2010, 18, 4991]. Based on the previous results, we designed and synthesized a new series of metronidazole acid acyl sulfonamide derivatives and a new series of phenylacetyl benzenesulfonamide derivatives and their anticancer activities were evaluated as potential EGFR and HER-2 kinase inhibitors. Among all the compounds, compound 12 displayed the most potent inhibitory activity EGFR and HER-2 (IC(50) = 0.39 mu M for EGFR and IC(50) = 1.53 mu M for HER-2) and it also showed the most potent growth inhibitory activity against A549 and B16-F10 cancer cell line in vitro, with an IC(50) value of 1.26 mu g/mL for A549 and 0.35 mu g/mL for B16-F10. Docking simulation was further performed to position compound 12 into the EGFR active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.038

文献信息

• Metronidazole acid acyl sulfonamide: A novel class of anticancer agents and potential EGFR tyrosine kinase inhibitors
  作者：Yin Luo、Yao Li、Ke-Ming Qiu、Xiang Lu、Jie Fu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.08.038

  日期：2011.10

  A series of novel metronidazole derivatives were recently reported as potent anticancer agents targeting EGFR and HER-2 by our group [Qian, Y.; Zhang, H. J.; Zhang, H.; Xu, C.; Zhao, J.; Zhu, H. L Bioorg. Med. Chem. 2010, 18, 4991]. Based on the previous results, we designed and synthesized a new series of metronidazole acid acyl sulfonamide derivatives and a new series of phenylacetyl benzenesulfonamide derivatives and their anticancer activities were evaluated as potential EGFR and HER-2 kinase inhibitors. Among all the compounds, compound 12 displayed the most potent inhibitory activity EGFR and HER-2 (IC(50) = 0.39 mu M for EGFR and IC(50) = 1.53 mu M for HER-2) and it also showed the most potent growth inhibitory activity against A549 and B16-F10 cancer cell line in vitro, with an IC(50) value of 1.26 mu g/mL for A549 and 0.35 mu g/mL for B16-F10. Docking simulation was further performed to position compound 12 into the EGFR active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.