(Z)-ethyl 2-(4-(benzyloxy)phenyl)-3-(4-chlorophenylamino)acrylate | 1321840-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-ethyl 2-(4-(benzyloxy)phenyl)-3-(4-chlorophenylamino)acrylate
• 英文别名: ethyl (Z)-3-(4-chloroanilino)-2-(4-phenylmethoxyphenyl)prop-2-enoate
• CAS: 1321840-48-5
• 化学式: C₂₄H₂₂ClNO₃
• 分子量: 407.897
• InChiKey: WDKKIRQWNCTKKE-KQWNVCNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苄氧基苯基乙酸乙酯 在 sodium hydride 作用下， 以 乙醇 为溶剂， 生成 (E)-ethyl 2-(4-(benzyloxy)phenyl)-3-(4-chlorophenylamino)acrylate 、 (Z)-ethyl 2-(4-(benzyloxy)phenyl)-3-(4-chlorophenylamino)acrylate
  参考文献：
  名称：

  Discovery of vinylogous carbamates as a novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  beta-Ketoacyl-acyl carrier protein synthase III (FabH) catalyzes the initial step of fatty acid biosynthesis via a type II fatty acid synthase in most bacteria. The important role of this essential enzyme combined with its unique structural features and ubiquitous occurrence in bacteria has made it an attractive new target for the development of new FabH inhibitors. We first used a structure-based approach to develop 24 new vinylogous carbamates (4a-15a, 4b-15b) that target FabH for the development of new antibiotics in this paper. Potent FabH inhibitory and selective anti-Gram-negative bacteria activities were observed in most of these vinylogous carbamates. Especially, compound 6a and 7a showed the most potent FabH inhibitory activity with IC(50) of 2.6 and 3.3 mu M, respectively. Docking simulation was performed to position compound 6a into the Escherichia coli FabH active site and the possible binding conformation of compounds has been proposed. The biological data and molecular docking indicated that compounds 6a and 7a were potent inhibitors of E. coli FabH as antibiotics deserving further research. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.048

文献信息

• Discovery of vinylogous carbamates as a novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors
  作者：Huan-Qiu Li、Yin Luo、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.06.048

  日期：2011.8

  beta-Ketoacyl-acyl carrier protein synthase III (FabH) catalyzes the initial step of fatty acid biosynthesis via a type II fatty acid synthase in most bacteria. The important role of this essential enzyme combined with its unique structural features and ubiquitous occurrence in bacteria has made it an attractive new target for the development of new FabH inhibitors. We first used a structure-based approach to develop 24 new vinylogous carbamates (4a-15a, 4b-15b) that target FabH for the development of new antibiotics in this paper. Potent FabH inhibitory and selective anti-Gram-negative bacteria activities were observed in most of these vinylogous carbamates. Especially, compound 6a and 7a showed the most potent FabH inhibitory activity with IC(50) of 2.6 and 3.3 mu M, respectively. Docking simulation was performed to position compound 6a into the Escherichia coli FabH active site and the possible binding conformation of compounds has been proposed. The biological data and molecular docking indicated that compounds 6a and 7a were potent inhibitors of E. coli FabH as antibiotics deserving further research. (C) 2011 Elsevier Ltd. All rights reserved.