2-(2-fluoro-benzyloxy)benzoic acid methyl ester | 1039068-83-1

• 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-(2-fluoro-benzyloxy)benzoic acid methyl ester
• 英文别名: Methyl 2-[(2-fluorophenyl)methoxy]benzoate；methyl 2-[(2-fluorophenyl)methoxy]benzoate
• CAS: 1039068-83-1
• 化学式: C₁₅H₁₃FO₃
• 分子量: 260.265
• InChiKey: NRWMAKAWPNLNDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-fluoro-benzyloxy)benzoic acid methyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-[(2-Fluorobenzyl)oxy]benzoic acid
  参考文献：
  名称：

  Design, synthesis and molecular docking of salicylic acid derivatives containing metronidazole as a new class of antimicrobial agents

  摘要：

  A series of novel salicylic acid derivatives containing metronidazole as Staphylococcus aureus Tyrosyl-tRNA synthetase (TyrRS) inhibitors have been synthesized and evaluated their biology activities as potential antibacterial agents. Among these compounds, compound 5r exhibited the most potent antibacterial activity against Gram-positive (S. aureus ATCC 6538 and Bacillus subtilis ATCC 6633) and Gram-negative (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) with MICs of 0.39-1.57 mu g/mL and showed the most potent S. aureus Tyrosyl-tRNA synthetase inhibitory with 2.3 mu M. Docking simulation was performed to insert compound 5r into the crystal structure of S. aureus Tyrosyl-tRNA synthetase active site to determine the probable binding model. These results suggested that compound 5r may be a promising antibacterial agent. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.075
• 作为产物：
  描述：

  2-氟溴苄 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-(2-fluoro-benzyloxy)benzoic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and molecular docking of salicylic acid derivatives containing metronidazole as a new class of antimicrobial agents

  摘要：

  A series of novel salicylic acid derivatives containing metronidazole as Staphylococcus aureus Tyrosyl-tRNA synthetase (TyrRS) inhibitors have been synthesized and evaluated their biology activities as potential antibacterial agents. Among these compounds, compound 5r exhibited the most potent antibacterial activity against Gram-positive (S. aureus ATCC 6538 and Bacillus subtilis ATCC 6633) and Gram-negative (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) with MICs of 0.39-1.57 mu g/mL and showed the most potent S. aureus Tyrosyl-tRNA synthetase inhibitory with 2.3 mu M. Docking simulation was performed to insert compound 5r into the crystal structure of S. aureus Tyrosyl-tRNA synthetase active site to determine the probable binding model. These results suggested that compound 5r may be a promising antibacterial agent. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.075

文献信息

• Design and Synthesis of New 2-Substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as Anticonvulsant Agents
  作者：Afshin Zarghi、Zahra Hajimahdi、Shohreh Mohebbi、Hootesa Rashidi、Sasan Mozaffari、Sahar Sarraf、Mehrdad Faizi、Seyed Abbas Tabatabaee、Abbas Shafiee

  DOI：10.1248/cpb.56.509

  日期：——

  A new series of 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles was designed and synthesized as anticonvulsant agents. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that the introduction of an amino group at position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at ortho position of benzyloxy moiety had the best anticonvulsant activity. Our results showed that this effect is mediated through benzodiazepine receptors mechanism.

  设计并合成了一系列新的 2-取代-5-[2-(2-卤苄氧基)苯基]-1,3,4-恶二唑，作为抗惊厥剂。电击和戊四唑诱导的致死性惊厥试验表明，在 1,3,4-oxadiazole 环的第 2 位引入一个氨基和在苄氧基的正交位置引入一个氟取代基具有最佳的抗惊厥活性。我们的研究结果表明，这种作用是通过苯并二氮杂卓受体机制介导的。