(S)-2-((Z)-5-(4-formylbenzylidene)-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: (S)-2-((Z)-5-(4-formylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(5Z)-5-[(4-formylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
• 化学式: C₂₀H₁₅NO₄S₂
• 分子量: 397.475
• InChiKey: HBERVVWREHRMPE-FDIDWWNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((Z)-5-(4-formylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 、 4-氨基-5-(2-溴苯基)-4H-1,2,4-噻唑-3-硫醇 在 溶剂黄146 作用下， 以80%的产率得到(S)-{(5Z)-5-[4-({[3-(2-bromophenyl)-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]imino}methyl)benzylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety

  摘要：

  Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 mu g/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 mu g/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 mu g/ml. All of the compounds synthesized in the current Letter were characterized by H-1 NMR, C-13 NMR, infrared and mass spectroscopy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.081
• 作为产物：
  描述：

  L-苯丙氨酸 在 哌啶 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (S)-2-((Z)-5-(4-formylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety

  摘要：

  Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 mu g/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 mu g/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 mu g/ml. All of the compounds synthesized in the current Letter were characterized by H-1 NMR, C-13 NMR, infrared and mass spectroscopy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.081

文献信息

• Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety
  作者：Chao Li、Jia-Chun Liu、Ya-Ru Li、Cheng Gou、Mei-Ling Zhang、Hong-Yan Liu、Xiao-Zhen Li、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2015.04.081

  日期：2015.8

  Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 mu g/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 mu g/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 mu g/ml. All of the compounds synthesized in the current Letter were characterized by H-1 NMR, C-13 NMR, infrared and mass spectroscopy. (C) 2015 Elsevier Ltd. All rights reserved.