ethyl 2-((5,6-di-p-tolyl-1,2,4-triazin-3-yl)thio)acetate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-((5,6-di-p-tolyl-1,2,4-triazin-3-yl)thio)acetate
• 英文别名: ethyl 2-[[5,6-bis(4-methylphenyl)-1,2,4-triazin-3-yl]sulfanyl]acetate
• 化学式: C₂₁H₂₁N₃O₂S
• 分子量: 379.483
• InChiKey: MQFWHMLAVKDKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4'-二甲基联苯甲酰 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 10.33h， 生成 ethyl 2-((5,6-di-p-tolyl-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

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.