(E)-4-fluoro-2-(((4-hydroxyphenethyl)imino)methyl)phenol | 1246463-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-fluoro-2-(((4-hydroxyphenethyl)imino)methyl)phenol
• 英文别名: (E)-4-fluoro-2-((4-hydroxyphenethylimino)methyl)phenol
• CAS: 1246463-57-9
• 化学式: C₁₅H₁₄FNO₂
• 分子量: 259.28
• InChiKey: FEOPHJJMULHJRT-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  对羟基苯乙胺 、 5-氟水杨醛 以 甲醇 为溶剂， 以83%的产率得到(E)-4-fluoro-2-(((4-hydroxyphenethyl)imino)methyl)phenol
  参考文献：
  名称：

  Design and synthesis of potent inhibitors of β-ketoacyl-acyl carrier protein synthase III (FabH) as potential antibacterial agents

  摘要：

  Twenty new Schiff bases were synthesized by reacting 5-fluoro-salicylaldehyde and primary amine as potent inhibitors of FabH. These compounds were assayed for antibacterial activity against Escherichia coli, Pseudomonas fluorescence, Bacillus subtilis and Staphylococcus aureus. Compounds with potent antibacterial activities were tested for their E. coli FabH inhibitory activity. (E)-4-fluoro-2-((4-hydroxyphenethylimino)methyl)phenol (10) showed the most potent antibacterial activity with MIC of 1.56-6.25 mu g/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.7 mu M. Docking simulation was performed to position compound 10 into the E. coli FabH active site to determine the probable binding conformation. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.033

文献信息

• Ultrasonic synthesis of tyramine derivatives as novel inhibitors of <b>α</b>-glucosidase <i>in vitro</i>
  作者：Hina Siddiqui、Muhammad Arslan Bashir、Kulsoom Javaid、Arsalan Nizamani、Huma Bano、Sammer Yousuf、Atta-ur Rahman、M. Iqbal Choudhary

  DOI：10.3109/14756366.2016.1142983

  日期：2016.11.1

  Tyramine derivatives 3-27 were synthesized by using conventional and environmental friendly ultrasonic techniques. These derivatives were then evaluated for the first time for their a-glucosidase (Sources: Saccharomyces cerevisiae and mammalian rat-intestinal acetone powder) inhibitory activity by using in vitro mechanism-based biochemical assays. Compounds 7, 14, 20, 21 and 26 were found to be more active (IC50 = 49.7 +/- 0.4, 318.8 +/- 3.7, 23.5 +/- 0.9, 302.0 +/- 7.3 and 230.7 +/- 4.0 mu M, respectively) than the standard drug, acarbose (IC50 = 840.0 +/- 1.73 mu M (observed) and 780 +/- 0.028 mu M (reported)) against alpha-glucosidase obtained from Saccharomyces cerevisiae. Kinetic studies were carried out on the most active members of the series in order to determine their mode of inhibition and dissociation constants. Compounds 7, 20 and 26 were found to be the competitive inhibitors of alpha-glucosidase. These compounds were also screened for their protein antiglycation, and dipeptidyl peptidase-IV (DPP-IV) inhibitory activities. Only compounds 20, 22 and 27 showed weak antiglycation activity with IC50 values 505.27 +/- 5.95, 581.87 +/- 5.50 and 440.58 +/- 2.74 mu M, respectively. All the compounds were found to be inactive against DDP-IV enzyme. Inhibition of alpha-glucosidase, DPP-IV enzymes and glycation of proteins are valid targets for the discovery of antidiabetic drugs. Cytotoxicity of compounds 3-27 was also evaluated by using mouse fibroblast 3T3 cell lines. All the compounds were found to be noncytotoxic. The current study describes the synthesis alpha-glucosidase inhibitory activity of derivatives, based on a natural product tyramine template. The compounds reported here may serve as the starting point for the design and development of novel alpha-glucosidase inhibitors as antidiabetic agents.
• Design and synthesis of potent inhibitors of β-ketoacyl-acyl carrier protein synthase III (FabH) as potential antibacterial agents
  作者：Lei Shi、Rui-Qin Fang、Zhen-Wei Zhu、Ying Yang、Kui Cheng、Wei-Qing Zhong、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.05.033

  日期：2010.9

  Twenty new Schiff bases were synthesized by reacting 5-fluoro-salicylaldehyde and primary amine as potent inhibitors of FabH. These compounds were assayed for antibacterial activity against Escherichia coli, Pseudomonas fluorescence, Bacillus subtilis and Staphylococcus aureus. Compounds with potent antibacterial activities were tested for their E. coli FabH inhibitory activity. (E)-4-fluoro-2-((4-hydroxyphenethylimino)methyl)phenol (10) showed the most potent antibacterial activity with MIC of 1.56-6.25 mu g/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.7 mu M. Docking simulation was performed to position compound 10 into the E. coli FabH active site to determine the probable binding conformation. (C) 2010 Elsevier Masson SAS. All rights reserved.