2-(3,4-dichlorophenyl)imino-1,3-thiazolidin-4-one | 101869-80-1

• 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: 2-(3,4-dichlorophenyl)imino-1,3-thiazolidin-4-one
• 英文别名: 2-(3,4-dichlorophenylimino)thiazolidin-4-one；2-<3,4-Dichlor-phenylimino>-thiazolidon-(4)；2-[(3,4-Dichlorophenyl)amino]-4(5H)-thiazolone
• CAS: 101869-80-1
• 化学式: C₉H₆Cl₂N₂OS
• 分子量: 261.131
• InChiKey: IWHBLKSEBCKYMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dichlorophenyl)imino-1,3-thiazolidin-4-one 、 3-(4-氟-苯基)-1-苯基-1H-吡唑-4-甲醛 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以66%的产率得到2-(3,4-dichlorophenylimino)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one
  参考文献：
  名称：

  2-(3,4-Dichlorophenylimino)-5-((3-(p -substitutedphenyl)-1-phenyl-1H -pyrazol-4-yl)methylene)thiazolidin-4-one as an Antibacterial, Antifungal and Antimycobacterial Agent

  摘要：

  2‐(3,4‐Dichlorophenylimino)‐5‐((3‐(p‐substitutedphenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)methylene) thiazolidin‐4‐one has been selected as a target bio‐active molecules. Newly synthesized compounds were screened with Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) for antibacterial, Candida albicans (MTCC 227), Aspergillus niger (MTCC 282), Aspergillus clavatus (MTCC 1323) for antifungal activity and H37Rv for antimycobacterial activity. Compounds 3a, 3c, 3d, 3e, and 3h are potentially active against Staphylococcus aureus, while 3h is active against C. albicans. Compounds 3d and 3f are active against H37Rv for mycobacterium tuberculosis. Other possesses moderate to good activity. The structures of synthesized compounds were firmly established by well‐defined elemental analyses (C, H, N, S/O) and spectral analysis technique likes, IR, 1H NMR and GC–MS.

  DOI：

  10.1002/jhet.2889
• 作为产物：
  描述：

  3,4-二氯苯胺 在 盐酸 、 sodium acetate 、 溶剂黄146 作用下， 反应 12.0h， 生成 2-(3,4-dichlorophenyl)imino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  2-(3,4-Dichlorophenylimino)-5-((3-(p -substitutedphenyl)-1-phenyl-1H -pyrazol-4-yl)methylene)thiazolidin-4-one as an Antibacterial, Antifungal and Antimycobacterial Agent

  摘要：

  2‐(3,4‐Dichlorophenylimino)‐5‐((3‐(p‐substitutedphenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)methylene) thiazolidin‐4‐one has been selected as a target bio‐active molecules. Newly synthesized compounds were screened with Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) for antibacterial, Candida albicans (MTCC 227), Aspergillus niger (MTCC 282), Aspergillus clavatus (MTCC 1323) for antifungal activity and H37Rv for antimycobacterial activity. Compounds 3a, 3c, 3d, 3e, and 3h are potentially active against Staphylococcus aureus, while 3h is active against C. albicans. Compounds 3d and 3f are active against H37Rv for mycobacterium tuberculosis. Other possesses moderate to good activity. The structures of synthesized compounds were firmly established by well‐defined elemental analyses (C, H, N, S/O) and spectral analysis technique likes, IR, 1H NMR and GC–MS.

  DOI：

  10.1002/jhet.2889

文献信息

• 一种5-(1H-吲哚-3-亚甲基)-1,3-噻唑烷-4- 酮类衍生物及其合成方法和应用
  申请人：西安交通大学

  公开号：CN104059060B

  公开（公告）日：2017-08-01

  一种5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用，以乙醇和或水为溶剂，将取代2‑取代亚氨基‑1,3‑噻唑烷‑4‑酮与1H‑吲哚‑3‑甲醛在哌啶催化条件下，回流反应，通过分子间脱水缩合反应形成亚甲基连接基，得到5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物。其中所涉及的中间体2‑取代亚氨基噻唑烷‑4‑酮是由各种单取代的硫脲氯乙酸乙酯或氯乙酸在低沸点溶剂中经回流条件下的环合反应制备而得，中间体2‑取代亚氨基‑3‑取代‑1,3,‑噻唑烷‑4‑酮由各种双取代的对称硫脲和氯乙酸通过绿色环保合成工艺制备。对所有目标化合物在酶分子水平上的生物活性初步筛选实验结果显示，目标产物对PTP1B和CDC25B在不同程度上显示一定的抑制活性。