5,6-di(thiophen-2-yl)-1,2,4-triazine-3-thiol | 1478981-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5,6-di(thiophen-2-yl)-1,2,4-triazine-3-thiol
• 英文别名: 5,6-dithiophen-2-yl-2H-1,2,4-triazine-3-thione
• CAS: 1478981-86-0
• 化学式: C₁₁H₇N₃S₃
• 分子量: 277.395
• InChiKey: IBIHJCNSUOYWQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-di(thiophen-2-yl)-1,2,4-triazine-3-thiol 、 氯乙酸乙酯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以86%的产率得到ethyl 2-((5,6-di(thiophen-2-yl)-1,2,4-triazin-3-yl)thio)acetate
  参考文献：
  名称：

  Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity

  摘要：

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.

  DOI：

  10.1007/s00044-017-2003-x
• 作为产物：
  描述：

  噻吩偶姻 、 氨基硫脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 5,6-di(thiophen-2-yl)-1,2,4-triazine-3-thiol
  参考文献：
  名称：

  Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity

  摘要：

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.

  DOI：

  10.1007/s00044-017-2003-x

文献信息

• Microwave-assisted synthesis and anticonvulsant activity of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives
  作者：Hamid Irannejad、Nima Naderi、Saeed Emami、Roja Qobadi Ghadikolaei、Alireza Foroumadi、Tina Zafari、Ali Mazar-Atabaki、Sakineh Dadashpour

  DOI：10.1007/s00044-013-0843-6

  日期：2014.5

  A series of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives were synthesized through microwave-promoted chemistry by condensation of the aromatic 1,2-diketones and thiosemicarbazide in a mixed green solvent. Subsequently, S-alkylation of 1,2,4-triazine-3-thiols afforded S-substituted derivatives. The anticonvulsant activity of the synthesized compounds was evaluated in vivo by electroshock and pentylenetetrazole (PTZ)-induced seizures tests. Among them, compound 4a bearing 4-pyridylmethylthio moiety on the triazine ring showed the highest protection in both electroshock and PTZ-induced seizures tests. Compound 4a showed no sign of neurotoxicity at the dose of 100 mg/kg in both rotarod and chimney tests.
• Anticonvulsant activity of 1,2,4-triazine derivatives with pyridyl side chain: synthesis, biological, and computational study
  作者：Hamid Irannejad、Hamid Nadri、Nima Naderi、Seyedeh Nesa Rezaeian、Neda Zafari、Alireza Foroumadi、Mohsen Amini、Mehdi Khoobi

  DOI：10.1007/s00044-014-1315-3

  日期：2015.6

  A series of 5,6-bisaryl-1,2,4-triazine-3-thiol-substituted derivatives were synthesized by condensation of 1,2-diketones and thiosemicarbazide under microwave irradiations and subsequent alkylation of thiol group by chloromethylpyridinium chloride. Evaluation of anticonvulsant activity of compounds was performed by maximal electroshock and pentylenetetrazole-induced seizures tests. In order to evaluate their neuroprotective potential, the ability of compounds to inhibit soybean 15-lipoxygenase was also assessed. Further molecular modeling and docking study on Na+ channel and GABA(A) receptor was performed to elucidate their mechanisms of action and necessary interactions in the active site. Compounds 2c and 2d with bis(4-bromophenyl) and pyridyl substituents showed highest protection up to 70 and 80 % in PTZ and MES-induced seizures, respectively, compared to the control group. Molecular docking study revealed their possible antiseizure mechanism of action through GABA(A) receptor, and in silico assessment of their BBB permeability indicated them as CNS active agents.
• WO2023/168240
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity
  作者：Tuba Tuylu Kucukkilinc、Kamaledin Safari Yanghagh、Beyza Ayazgok、Mohammad Ali Roknipour、Farshad Homayouni Moghadam、Alireza Moradi、Saeed Emami、Mohsen Amini、Hamid Irannejad

  DOI：10.1007/s00044-017-2003-x

  日期：2017.11

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.