2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one
• 英文别名: 2-(5-methyl-1,3,4-thiadiazol-2-ylimino)-thiazolidin-4-one；(2E)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one
• 化学式: C₆H₆N₄OS₂
• 分子量: 214.272
• InChiKey: IGDKXVLFRWIDKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  五氟苯甲醛 、 2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one 在 sodium methylate 、 溶剂黄146 作用下， 反应 24.0h， 以76.5%的产率得到(5Z)-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-5-[(pentafluorophenyl)-methylidene]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent

  摘要：

  Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 mu M, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 mu M, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.

  DOI：

  10.1016/j.bioorg.2020.103657
• 作为产物：
  描述：

  氯乙酸 、 (5-甲基-1,3,4-噻二唑-2-基)硫脲 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  A Synthetic Approach, Characterization and Biological Evaluation of Novel 5-(Arylidene)-2-(5-methyl-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one Derivatives

  摘要：

  利用串联管稀释法对合成的衍生物进行了抗微生物潜力筛选。结果显示，所有合成的化合物对被测试的微生物具有显著的生物活性。化合物TA2、TA3、TA4、TA9、TA10和TA20对被测试的微生物菌株具有很好的抗菌活性。化合物TA4（2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)-5-(4-硝基苄亚甲基)-噻唑烷-4-酮）和TA2（5-(4-氯苄亚甲基)-2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)噻唑烷-4-酮）显示出对微生物菌株有很好的抗菌活性。化合物TA9（5-(4-(苄氧基)苄亚甲基)-2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)噻唑烷-4-酮）对枯草杆菌最有效。化合物TA10（5-(3,4-二甲氧基苄亚甲基)-2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)噻唑烷-4-酮）被发现对革兰氏阴性细菌最具潜力。化合物TA3（5-(4-溴苄亚甲基)-2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)噻唑烷-4-酮）和TA20（5-(2-溴苄亚甲基)-2-((5-甲基-1,3,4-噻二唑-2-基)亚胺)噻唑烷-4-酮）是对真菌菌株最有效的化合物。

  DOI：

  10.14233/ajchem.2021.23203

文献信息

• ——
  作者：M. Kidwai、A. D. Mishra

  DOI：10.1023/a:1025649227322

  日期：——

  Novel 2-(5-R-1,3,4-thiadiazol-2-yl)aminothiazolin-4-ones 6a-h and 2-imino-3-(5-R-1,3,4-thiadiazol-2-yl)thiazolidin-4-ones 7a-h were prepared by treating N-(5-R-1,3,4-thiadiazol-2-yl)thioureas 4a-h with chloroacetic acid on various solid supports under microwave irradiation. Tautomeric mixtures of compounds 6a-h and 7a-h were obtained in all cases. In alkaline and neutral media, compounds 6a-h were the major products, while ill acid media, 7a-h were the major products.