3-[(4-benzylpiperazin-1-yl)methyl]-5-(pyridin-4-yl)-1,3,4-oxadiazole-2(3H)-thione

• 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: 3-[(4-benzylpiperazin-1-yl)methyl]-5-(pyridin-4-yl)-1,3,4-oxadiazole-2(3H)-thione
• 英文别名: 3-[(4-Benzylpiperazin-1-yl)methyl]-5-(4-pyridyl)-1,3,4-oxadiazole-2-thione；3-[(4-benzylpiperazin-1-yl)methyl]-5-pyridin-4-yl-1,3,4-oxadiazole-2-thione
• 化学式: C₁₉H₂₁N₅OS
• mdl: MFCD03820765
• 分子量: 367.475
• InChiKey: ONGRDHJSYYTAKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-苄基哌嗪 、 5-(4-吡啶基)-1,3,4-二唑-2-硫醇 在 聚合甲醛 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以58%的产率得到3-[(4-benzylpiperazin-1-yl)methyl]-5-(pyridin-4-yl)-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  Mannich base derivatives of 1,3,4-oxadiazole: synthesis and screening against Entamoeba histolytica

  摘要：

  Mannich base derivatives of 5-(pyridine-4-yl)-1,3,4-oxadiazole-2-(3H)-thione with substituted piperazine were synthesized and characterized. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica and the cytotoxicity of the compounds having IC50 value less than metronidazole was assessed by MTT assay on human breast cancer MCF-7 cell line. The results revealed that compounds 2, 3 and 5 were found to be better inhibitors of E. histolytica than the reference drug metronidazole and found low cytotoxic in the concentration range of 2.5-250 mu M. This study suggests the possibility of developing 1,3,4-oxadiazole analogues as potential drug candidates.

  DOI：

  10.1007/s00044-012-0108-9

文献信息

• Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations
  作者：Maria Grazia Mamolo、Daniele Zampieri、Luciano Vio、Maurizio Fermeglia、Marco Ferrone、Sabrina Pricl、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.bmc.2005.03.013

  日期：2005.6

  4-oxadiazol-2-one derivatives were synthesized and tested for their in vitro antimycobacterial activity. Oxadiazolone derivatives showed an interesting antimycobacterial activity against the tested strain of Mycobacterium tuberculosis H(37)Rv, whereas the corresponding thione derivatives were devoid of activity. Molecular modeling investigations showed that the active compounds may interact at the active site of

  合成了3H-1,3,4-恶二唑-2-硫酮和3H-1,3,4-恶二唑-2-酮衍生物并测试了其体外抗分枝杆菌活性。恶二唑酮衍生物对测试的结核分枝杆菌H（37）Rv菌株显示出有趣的抗分枝杆菌活性，而相应的硫酮衍生物则没有活性。分子模型研究表明，活性化合物可能在固醇生物合成途径中的分枝杆菌细胞色素P450依赖性固醇14α-脱甲基酶的活性位点相互作用，并且它们的结合自由能值与其MIC值一致。