(Z)-2-(4-oxo-5-((5-phenylfuran-2-yl)methylene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid | 1440969-11-8

• 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: (Z)-2-(4-oxo-5-((5-phenylfuran-2-yl)methylene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(5Z)-4-oxo-5-[(5-phenylfuran-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
• CAS: 1440969-11-8
• 化学式: C₂₃H₁₇NO₄S₂
• 分子量: 435.524
• InChiKey: ZHUOVFXBENXOMC-HJHGFDQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯胺 在 哌啶 、 盐酸 、 溶剂黄146 、 copper dichloride 、 sodium nitrite 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 17.0h， 生成 (Z)-2-(4-oxo-5-((5-phenylfuran-2-yl)methylene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety

  摘要：

  Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 mu g/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 mu g/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by H-1 and C-13 NMR, infrared, and mass spectroscopy.

  DOI：

  10.1007/s00044-013-0648-7

文献信息

• Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety
  作者：Jian Che、Chang-Ji Zheng、Ming-Xia Song、Ya-Jing Bi、Yi Liu、Yin-Jing Li、Yan Wu、Liang-Peng Sun、Hu-Ri Piao

  DOI：10.1007/s00044-013-0648-7

  日期：2014.1

  Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 mu g/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 mu g/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by H-1 and C-13 NMR, infrared, and mass spectroscopy.