sodium m-trifluoromethylbenzoate | 69226-41-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: sodium m-trifluoromethylbenzoate
• 英文别名: Sodium 3-(trifluoromethyl)benzoate；sodium;3-(trifluoromethyl)benzoate
• CAS: 69226-41-1
• 化学式: C₈H₄F₃O₂*Na
• 分子量: 212.104
• InChiKey: FETAXBXCYXFUNC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P305+P351+P338,P261
• 危险性描述：
  H319,H332,H302,H315,H335

反应信息

• 作为反应物：
  描述：

  、 sodium m-trifluoromethylbenzoate 以 二甲基亚砜 为溶剂， 以71.2%的产率得到4-(2-(3-trifluoromethylphenylformyoxyl)ethoxy)-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

  3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

  摘要：

  Thirty-eight 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones were designed, prepared and tested for antibacterial activities. Some of them showed significant antibacterial activity against Gram-positive organism, Gram-negative organism and fungus. Out of these compounds, 4-(2-(3-chlorophenylformyloxy)ethoxy)-3-(4-chlorophenyl)furan-2(5H)-one (d40) showed the widest spectrum of activity with MIC50 of 2.0 mu g/mL against Staphylococcus aureus, 4.3 mu g/mL against Escherichia coli, 1.5 mu g/mL against Pseudomonas aeruginosa and 1.2 mu g/mL against Candida albicans. Our data disclosed that MIC50 values against whole cell bacteria are positive correlation with MIC50 values against tyrosyl-tRNA synthetase. Meanwhile, molecular docking of d40 into S. aureus tyrosyl-tRNA synthetase active site was also performed, and the inhibitor tightly fitting the active site might be an important reason why it has high antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.066
• 作为试剂：
  描述：

  3-三氟甲基苯甲酸 在 氯化亚砜 、 sodium m-trifluoromethylbenzoate 作用下， 反应 15.0h， 生成 3-methoxy-8-allyl-3'-trifluoromethylflavone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid

  摘要：

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.

  DOI：

  10.1021/jm030771o

文献信息

• 3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation
  作者：Xu-Dong Wang、Rui-Cheng Deng、Jing-Jun Dong、Zhi-Yun Peng、Xiao-Ming Gao、Shu-Ting Li、Wan-Qiang Lin、Chun-Lei Lu、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.06.066

  日期：2013.9

  Thirty-eight 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones were designed, prepared and tested for antibacterial activities. Some of them showed significant antibacterial activity against Gram-positive organism, Gram-negative organism and fungus. Out of these compounds, 4-(2-(3-chlorophenylformyloxy)ethoxy)-3-(4-chlorophenyl)furan-2(5H)-one (d40) showed the widest spectrum of activity with MIC50 of 2.0 mu g/mL against Staphylococcus aureus, 4.3 mu g/mL against Escherichia coli, 1.5 mu g/mL against Pseudomonas aeruginosa and 1.2 mu g/mL against Candida albicans. Our data disclosed that MIC50 values against whole cell bacteria are positive correlation with MIC50 values against tyrosyl-tRNA synthetase. Meanwhile, molecular docking of d40 into S. aureus tyrosyl-tRNA synthetase active site was also performed, and the inhibitor tightly fitting the active site might be an important reason why it has high antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.