N-benzylidene-N'-[3-(4-nitrophenyl)-5-thiophen-2-yl-3H-[1,3,4]thiadiazol-2-ylidene]hydrazine | 1243671-59-1

• 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: N-benzylidene-N'-[3-(4-nitrophenyl)-5-thiophen-2-yl-3H-[1,3,4]thiadiazol-2-ylidene]hydrazine
• 英文别名: 2-(benzylidenehydrazono)-3-(4-nitrophenyl)-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-thiadiazole
• CAS: 1243671-59-1
• 化学式: C₁₉H₁₃N₅O₂S₂
• 分子量: 407.477
• InChiKey: MVYBILLCLPQAQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  benzaldehyde thiocarbohydrazone 、 N-(p-nitrophenyl)-C-(2-thienyl)formohydrazidoyl bromide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 N-benzylidene-N'-[3-(4-nitrophenyl)-5-thiophen-2-yl-3H-[1,3,4]thiadiazol-2-ylidene]hydrazine
  参考文献：
  名称：

  由碳硫二酰肼合成新型噻二唑和双噻二唑

  摘要：

  据报道，通过酰卤与碳硫二酰肼的反应可有效合成1,3,4-噻二唑和双噻二唑。另外，通过双-（取代的亚甲基）碳硫代二di的氧化环化获得1,2,4-三唑并[3,4- b ] [1,3,4]噻二唑。

  DOI：

  10.1016/j.tetlet.2010.06.060

文献信息

• 5-(Thiophen-2-yl)-1,3,4-thiadiazole derivatives: synthesis, molecular docking and in vitro cytotoxicity evaluation as potential anticancer agents
  作者：Sobhi Gomha、Mastoura Edrees、Zeinab Muhammad、Ahmed El-Reedy

  DOI：10.2147/dddt.s165276

  日期：——

  Background: Nowadays, cancer is an important public health problem in all countries. Limitations of current chemotherapy for neoplastic diseases such as severe adverse reactions and tumor resistance to the chemotherapeutic drugs have been led to a temptation for focusing on the discovery and development of new compounds with potential anticancer activity. The importance of thiophene and thiadiazole rings as scaffolds present in a wide range of therapeutic agents has been well reported and has driven the synthesis of a large number of novel antitumor agents.Methods: A series of new 1,3,4-thiadiazoles were synthesized by heterocyclization of N-(4nitrophenyl) thiophene-2-carbohydrazonoyl chloride with a variety of hydrazine-carbodithioate derivatives. The mechanisms of these reactions were discussed and the structure of the new products was elucidated via spectral data and elemental analysis. All the new synthesized compounds were investigated for in vitro activities against human hepatocellular carcinoma (HepG-2) and human lung cancer (A-549) cell lines compared with cisplatin standard anticancer drug. Moreover, molecular docking using MOE 2014.09 software was also carried out for the high potent compound 20b with the binding site of dihydrofolate reductase (DHFR, PDB ID (3NU0)).Results: The results showed that compound 20b has promising activities against HepG-2 and A-549 cell lines (IC50 value of 4.37 +/- 0.7 and 8.03 +/- 0.5 mu M, respectively) and the results of molecular docking supported the biological activity with total binding energy equals -1.6 E (Kcal/mol).Conclusion: Overall, we synthesized a new series of 1,3,4-thiadiazoles as potential antitumor agents against HepG-2 and A-549 cell lines.