N-[(E)-(3-bromophenyl)methylideneamino]-4-hydroxy-3-methoxybenzamide | 1415691-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[(E)-(3-bromophenyl)methylideneamino]-4-hydroxy-3-methoxybenzamide
• CAS: 1415691-67-6
• 化学式: C₁₅H₁₃BrN₂O₃
• 分子量: 349.184
• InChiKey: ZZPPGRBZEHLDPE-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香草酸甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 N-[(E)-(3-bromophenyl)methylideneamino]-4-hydroxy-3-methoxybenzamide
  参考文献：
  名称：

  Design, synthesis and antibacterial activities of vanillic acylhydrazone derivatives as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of acylhydrazone derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong broad-spectrum antibacterial activity. Compounds with potent antibacterial activities were tested for their Escherichia coli FabH inhibitory activity. Especially, compound E9 showed the most potent antibacterial activity with MIC values of 0.39-1.56 mu g/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.5 mu M. Docking simulation was performed to position compound E9 into the E. coli FabH active site to determine the probable binding conformation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.009

文献信息

• Design, synthesis and antibacterial activities of vanillic acylhydrazone derivatives as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors
  作者：Xiao-Liang Wang、Yan-Bin Zhang、Jian-Feng Tang、Yu-Shun Yang、Ruo-Qi Chen、Fei Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2012.09.009

  日期：2012.11

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of acylhydrazone derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong broad-spectrum antibacterial activity. Compounds with potent antibacterial activities were tested for their Escherichia coli FabH inhibitory activity. Especially, compound E9 showed the most potent antibacterial activity with MIC values of 0.39-1.56 mu g/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.5 mu M. Docking simulation was performed to position compound E9 into the E. coli FabH active site to determine the probable binding conformation. (C) 2012 Elsevier Masson SAS. All rights reserved.