5-((4-chlorophenyl)(phenylthio)methyl)-2-thioxothiazolidin-4-one | 1562112-75-7

• 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: 5-((4-chlorophenyl)(phenylthio)methyl)-2-thioxothiazolidin-4-one
• 英文别名: 5-[(4-Chlorophenyl)-phenylsulfanyl-methyl]-2-thioxo-thiazolidin-4-one；5-[(4-chlorophenyl)-phenylsulfanylmethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1562112-75-7
• 化学式: C₁₆H₁₂ClNOS₃
• 分子量: 365.928
• InChiKey: ZHXRUKAZSCFNQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 以 水 为溶剂， 生成 5-((4-chlorophenyl)(phenylthio)methyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  An efficient and green procedure for synthesis of rhodanine derivatives by aldol-thia-Michael protocol using aqueous diethylamine medium

  摘要：

  本研究介绍了一种在二乙胺水介质中采用串联醛醇缩合-噻-迈克尔加成法合成罗丹宁衍生物的简单、经济和绿色方法。实验方案操作简单，分离出的产物收率高至极佳（82-96%）。由于自发沉淀总是发生在过程的最后阶段，因此只需简单过滤即可轻松分离产物。

  DOI：

  10.1039/c3ra46551a

文献信息

• Synthesis, molecular structure investigations and antimicrobial activity of 2-thioxothiazolidin-4-one derivatives
  作者：Assem Barakat、Hany J. Al-Najjar、Abdullah Mohammed Al-Majid、Saied M. Soliman、Yahia Nasser Mabkhot、Mohamed H.M. Al-Agamy、Hazem A. Ghabbour、Hoong-Kun Fun

  DOI：10.1016/j.molstruc.2014.10.038

  日期：2015.2

  A variety of 2-thioxothiazolidin-4-one derivatives were prepared and their in vitro antimicrobial activities were studied. Most of these compounds showed significant antibacterial activity specifically against Gram-positive bacteria, among which compounds 4a,e,g, 5b,e,g,h and 6f exhibit high levels of antimicrobial activity against Bacillus subtilis ATCC 10400 with Minimum Inhibitory Concentration (MIC) value of 16 mu g/mL. All compounds have antifungal activity against Candida albicans. Unfortunately, however, none of the compounds were active against Gram-negative bacteria. The chemical structure of 3 was confirmed by X-ray single crystal diffraction technique. DFT calculations of 3 have been performed on the free C10H7Cl2NO2S2, 3a and the H-bonded complex, C10H7Cl2NO2S2 center dot H2O, 3b to explore the effect of the H-bonding interactions on the geometric and electronic properties of the studied systems. A small increase in bond length was observed in the C12-O6 due to the H-bonding interactions between 3a and water molecule. MEP study has been used to recognize the most reactive sites towards electrophilic and nucleophilic attacks as well as the possible sites for the H-bonding interactions. The TD-DFT calculations have been used to predict theoretically the electronic spectra of the studied compound. The most intense transition band is predicted at 283.9 nm due to the HOMO-2/HOMO-1 to LUMO transitions. NBO analyses were carried out to investigate the stabilization energy of the various intramolecular charge transfer interactions within the studied molecules. (C) 2014 Elsevier B.V. All rights reserved.