(Z)-2-amino-5-(4-nitrobenzylidene)thiazol-4(5H)-one | 36946-75-5

• 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: (Z)-2-amino-5-(4-nitrobenzylidene)thiazol-4(5H)-one
• 英文别名: 2-amino-5-(4-nitro-benzylidene)-thiazol-4-one；2-Amino-5-(4-nitro-benzyliden)-thiazol-4-on；(5Z)-2-imino-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
• CAS: 36946-75-5
• 化学式: C₁₀H₇N₃O₃S
• 分子量: 249.25
• InChiKey: KQCJDRGWZYGLDG-YVMONPNESA-N

物化性质

• 熔点：
  304 °C (decomp)
• 沸点：
  439.0±55.0 °C(predicted)
• 密度：
  1.60±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-amino-5-(4-nitrobenzylidene)thiazol-4(5H)-one 在 tin(II) chloride dihdyrate 、 三乙酰氧基硼氢化钠 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 38.67h， 生成 (R,Z)-2-(3-(((4-((2-imino-4-oxothiazolidin-5-ylidene)methyl)phenyl)amino)methyl)benzamido)pentanedioic acid
  参考文献：
  名称：

  Structure-Based Design of a New Series of d-Glutamic Acid Based Inhibitors of Bacterial UDP-N-acetylmuramoyl-l-alanine:d-glutamate Ligase (MurD)

  摘要：

  MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of D-glutamic acid-based Escherichia colt MurD inhibitors incorporating the 5-benzylidenethiazolidin-4-one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 mu M). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC50 values in the low micromolar range, represent the most potent D-Glu-based MurD inhibitors reported to date.

  DOI：

  10.1021/jm2002525
• 作为产物：
  描述：

  对硝基苯甲醛 、 假硫代乙内酰脲 在 sodium acetate 、 溶剂黄146 作用下， 反应 20.0h， 以90%的产率得到(Z)-2-amino-5-(4-nitrobenzylidene)thiazol-4(5H)-one
  参考文献：
  名称：

  Structure-Based Design of a New Series of d-Glutamic Acid Based Inhibitors of Bacterial UDP-N-acetylmuramoyl-l-alanine:d-glutamate Ligase (MurD)

  摘要：

  MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of D-glutamic acid-based Escherichia colt MurD inhibitors incorporating the 5-benzylidenethiazolidin-4-one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 mu M). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC50 values in the low micromolar range, represent the most potent D-Glu-based MurD inhibitors reported to date.

  DOI：

  10.1021/jm2002525

文献信息

• Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives
  作者：Wesam Shehab、Maged Aziz、Nourhan Elhoseni、Mohamed Assy、Magda Abdellattif、Eman Hamed

  DOI：10.3390/molecules27030767

  日期：——

  phenylhydrazine, and barbituric acid to yield 8, 9, 10, and 11, respectively. Using ascorbic acid as the standard compound, the pharmacological testing for antioxidant activity assessment of the produced derivatives was evaluated against ABTS (2,20-azinobis (3-ethylbenzothiazoline-6-sulfonic acid). Candidate 6 exhibited the best activity as an antioxidant agent compared to ascorbic acid as a reference compound

  在我们发现和开发与抗坏血酸和其他生物活性相比具有抗氧化作用的化合物的过程中，我们设计、合成和评估了一系列新的杂环部分药物 （1-11） 作为抗氧化剂和抗菌剂。作为起始部分，这些新的候选化合物来自两种有前途的杂环化合物，即咪唑丁-4-酮和噻唑-4-酮。首先，由于尿素、苯胺和氯乙酸在热条件下进行环缩合一锅三元反应，得到二苯基咪唑 1。从这种起始化合物中，我们可以设计和创造新的生命环，例如化合物 5 和 6 中的嘌呤和三嗪。其次，在乙酸钠存在下，硫脲、氯乙酸、对硝乙醛的分子间环化得到起始噻唑衍生物 7。我们通过使用不同的试剂（如苯胺、苯二胺、苯肼和巴比妥酸）合成了第二种起始化合物 7 的各种衍生物，分别得到 8、9、10 和 11。以抗坏血酸为标准化合物，对照 ABTS（2,20-氮杂乙噻唑啉-6-磺酸）评价所产生衍生物的抗氧化活性评估的药理学试验。与作为参考化合物的抗坏血酸相比，候选 6 作为
• Taniyama et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 154,157
  作者：Taniyama et al.

  DOI：——

  日期：——
• SOLOVEVA-YAVITS S. YU.; RAMSH S. M.; SMORYGO N. A.; GINAK A. I.; SOCHILIN+, XIMIYA GETEROTSIKL. SOED., 1980, HO 7, 929-932
  作者：SOLOVEVA-YAVITS S. YU.、 RAMSH S. M.、 SMORYGO N. A.、 GINAK A. I.、 SOCHILIN+

  DOI：——

  日期：——
• EL-SHAFEI, AHMED KAMAL;EL-SAYED, AHMED MAHMOUD;ABDEL-GHANY, HOSSAM;EL-SAG+, GAZZ. CHIM. ITAL., 120,(1990) N, C. 193-195
  作者：EL-SHAFEI, AHMED KAMAL、EL-SAYED, AHMED MAHMOUD、ABDEL-GHANY, HOSSAM、EL-SAG+

  DOI：——

  日期：——
• RAMSH, S. M.;SOLOVEVA, S. YU.;GINAK, A. I., XIMIYA GETEROTSIKL. SOEDIN., 1983, N 7, 928-932
  作者：RAMSH, S. M.、SOLOVEVA, S. YU.、GINAK, A. I.

  DOI：——

  日期：——