5,6-bis(4-bromophenyl)-1,2,4-triazine-3-thiol | 1478981-82-6

• 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-bis(4-bromophenyl)-1,2,4-triazine-3-thiol
• CAS: 1478981-82-6
• 化学式: C₁₅H₉Br₂N₃S
• 分子量: 423.131
• InChiKey: CXRGANQBXNXKFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-(4-chlorophenyl)thiazol-2-yl)acetamide 、 5,6-bis(4-bromophenyl)-1,2,4-triazine-3-thiol 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到2-((5,6-bis(4-bromophenyl)-1,2,4-triazin-3-yl)thio)-N-(4-(4-chlorophenyl)thiazol-2-yl)acetamide
  参考文献：
  名称：

  新型5,6-二芳基-1,2,4-三嗪噻唑衍生物作为新型α-葡萄糖苷酶抑制剂的合成，生物学评估和对接研究

  摘要：

  合成了新颖的5,6-二芳基-1,2,4-三嗪噻唑衍生物（7a - 7q），并通过1 H NMR和13 C NMR对其进行了表征，并评估了其对α-葡萄糖苷酶的抑制活性。与标准阿卡波糖（IC 50  = 817.38±6.27μM）相比，所有测试化合物均显示出良好的α-葡萄糖苷酶抑制活性，IC 50值在2.85±0.13和14.19± 0.23μM之间。化合物7i（IC 50 = 2.85±0.13μM）在这一系列化合物中表现出最高的活性。为了研究这类化合物与α-葡萄糖苷酶的结合方式，进行了分子对接研究。该研究表明，这些5,6-二芳基-1,2,4-三嗪噻唑衍生物是一类新的α-葡萄糖苷酶抑制剂。

  DOI：

  10.1016/j.bioorg.2018.03.015
• 作为产物：
  描述：

  4,4'-二溴联苯酰 、 氨基硫脲 在 溶剂黄146 作用下， 反应 3.0h， 生成 5,6-bis(4-bromophenyl)-1,2,4-triazine-3-thiol
  参考文献：
  名称：

  新型5,6-二芳基-1,2,4-三嗪噻唑衍生物作为新型α-葡萄糖苷酶抑制剂的合成，生物学评估和对接研究

  摘要：

  合成了新颖的5,6-二芳基-1,2,4-三嗪噻唑衍生物（7a - 7q），并通过1 H NMR和13 C NMR对其进行了表征，并评估了其对α-葡萄糖苷酶的抑制活性。与标准阿卡波糖（IC 50  = 817.38±6.27μM）相比，所有测试化合物均显示出良好的α-葡萄糖苷酶抑制活性，IC 50值在2.85±0.13和14.19± 0.23μM之间。化合物7i（IC 50 = 2.85±0.13μM）在这一系列化合物中表现出最高的活性。为了研究这类化合物与α-葡萄糖苷酶的结合方式，进行了分子对接研究。该研究表明，这些5,6-二芳基-1,2,4-三嗪噻唑衍生物是一类新的α-葡萄糖苷酶抑制剂。

  DOI：

  10.1016/j.bioorg.2018.03.015

文献信息

• 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.
• 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.
• Novel kojic acid-1,2,4-triazine hybrids as anti-tyrosinase agents: Synthesis, biological evaluation, mode of action, and anti-browning studies
  作者：Min He、Meiyan Fan、Wei Yang、Zhiyun Peng、Guangcheng Wang

  DOI：10.1016/j.foodchem.2023.136047

  日期：2023.3