1-(1-(pyridin-2-yl)ethylidene)-2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazine | 1416453-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1-(pyridin-2-yl)ethylidene)-2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazine
• 英文别名: (2-(1-(pyridin-2-yl)ethylene)hydrazinyl)-4-(4-fluorophenyl)-1,3-thiazole；4-(4-fluorophenyl)-N-(1-pyridin-2-ylethylideneamino)-1,3-thiazol-2-amine
• CAS: 1416453-57-0
• 化学式: C₁₆H₁₃FN₄S
• 分子量: 312.37
• InChiKey: CXJVEJWTPBZESY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.17
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 在 溶剂黄146 、 calcium carbonate 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 生成 1-(1-(pyridin-2-yl)ethylidene)-2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Study of in vitro biological activity of thiazoles on Leishmania (Leishmania) infantum

  摘要：

  Objectives: In the prospection of possible agents against neglected diseases, thiazole compounds are presented as promising candidates and are known to have activity against trypanosomatid parasites. Thus, this work aimed to evaluate the effects of thiazole compounds on Leishmania infantum, the aetiological agent of visceral leishmaniasis.Methods: Thiazole compounds (five thiazoacetylpyridines [TAPs-01, -04, -05, -06, -09) and five thiazopyridines [TPs-01, -04, -05, -06, -09]) were tested regarding their leishmanicidal activity on both promastigote and amastigote forms of L. infantum. Cytotoxicity was tested using peritoneal macrophages of BALB/c mice. Ultrastructural analyses were performed to identify possible intracellular targets of the most effective compound on promastigote forms. To observe routes that can clarify the possible mechanism of action of the compounds on the intracellular amastigote forms, the nitrite dosage was performed.Results: All compounds inhibited the growth of promastigote and presented low cytotoxicity, being more selective to the parasite than to mammalian cells. All compounds tested were able to decrease macrophage infection. There was a significant decrease in the survival rate of the amastigote when compared with the untreated cells, with TAP-04 presenting the best index. TAP-04 induced ultrastructural changes that are related to cell death by apoptosis. None of the macrophage groups infected with L. infantum and subsequently treated showed increased nitrite release.Conclusions: The low toxicity to mammalian cells and the leishmanicidal activity observed demonstrate that the synthesis of drugs based in thiosemicarbazone nucleus, thiazole and pyridine derivatives are promising for the treatment of visceral leishmaniasis. (C) 2020 The Authors. Published by Elsevier Ltd on behalf of International Society for Antimicrobial Chemotherapy.

  DOI：

  10.1016/j.jgar.2020.02.028