2-(5-(2-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(5-(2-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(5Z)-5-[(2-nitrophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
• 化学式: C₁₉H₁₄N₂O₅S₂
• 分子量: 414.463
• InChiKey: BIUFBZZZQKVFRJ-CNYBTUBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-2-(4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 、 邻硝基苯甲醛 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 以25%的产率得到2-(5-(2-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  The synthesis of phenylalanine-derived C5-substituted rhodanines and their activity against selected methicillin-resistant Staphylococcus aureus (MRSA) strains

  摘要：

  A series of rhodanine compounds containing various substituents at the N3- and C5-positions were synthesized and their in vitro activity against a panel of clinically relevant MRSA strains was determined. The anti-MRSA activity of compounds 21 (MIC = 3.9 mu g/mL, MBC = 7.8 mu g/mL) and 22 (MIC = 1.95 mu g/mL, MBC = 7.8 mu g/mL) was significantly greater than that of the lead compounds, 1-3 and reference antibiotics penicillin G (MIC = 31.25 mu g/mL) and ciprofloxacin (MIC = 7.8 mu g/mL) and comparable to that of vancomycin (MIC = 0.97 mu g/mL). Compounds 21 and 22 were found to be bactericidal at only 2-4-fold higher than their MIC concentrations. In addition, their MIC values remained unchanged in the presence or absence of 10% serum. Overall, the results suggest that compounds 21 and 22 may be of potential use in the treatment of MRSA infections. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.045