6-phenyl-2H-[1,2,4]triazine-3-thione | 27623-09-2

• 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: 6-phenyl-2H-[1,2,4]triazine-3-thione
• 英文别名: 6-Phenyl-2,3-dihydro-as-triazin-3-thion；6-phenyl-2H-1,2,4-triazine-3-thione
• CAS: 27623-09-2
• 化学式: C₉H₇N₃S
• 分子量: 189.241
• InChiKey: FSTKPYCQVNEYIO-UHFFFAOYSA-N

物化性质

• 沸点：
  297.4±23.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenyl-2H-[1,2,4]triazine-3-thione 在 肼 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 生成 3-hydrazino-6-phenyl-1,2,4-triazine
  参考文献：
  名称：

  Synthesis, biological activities, and molecular docking studies of triazolo[4,3‐b]triazine derivatives as a novel class of α‐glucosidase and α‐amylase inhibitors

  摘要：

  In diabetes mellitus, amylase and glucosidase enzymes are the primary triggers. The main function of these enzymes is to break macromolecules into simple sugar units, which directly affect blood sugar levels by increasing blood permeability. To overcome this metabolic effect, there is a need for a potent and effective inhibitor capable of suppressing the enzymatic conversion of sugar macromolecules into their smaller units. Herein, we reported the discovery of a series of substituted triazolo[4,3‐b][1,2,4]triazine derivatives as α‐glucosidase and α‐amylase inhibitors. All target compounds demonstrated significant inhibitory activities against α‐glucosidase and α‐amylase enzymes compared with acarbose as the positive control. The most potent compound 10k, 2‐[(6‐phenyl‐[1,2,4]triazolo[4,3‐b][1,2,4]triazin‐3‐yl)thio]‐N‐[4‐(trifluoromethyl)phenyl]acetamide, demonstrated IC₅₀ values of 31.87 and 24.64 nM against α‐glucosidase and α‐amylase enzymes, respectively. To study their mechanism of action, kinetic studies were also done, which determined the mode of inhibition of both enzymes. Molecular docking was used to confirm the binding interactions of the most active compounds.

  DOI：

  10.1002/ardp.202300628
• 作为产物：
  描述：

  3,4-二羟基苯乙酮 在 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-phenyl-2H-[1,2,4]triazine-3-thione
  参考文献：
  名称：

  Synthesis, biological activities, and molecular docking studies of triazolo[4,3‐b]triazine derivatives as a novel class of α‐glucosidase and α‐amylase inhibitors

  摘要：

  In diabetes mellitus, amylase and glucosidase enzymes are the primary triggers. The main function of these enzymes is to break macromolecules into simple sugar units, which directly affect blood sugar levels by increasing blood permeability. To overcome this metabolic effect, there is a need for a potent and effective inhibitor capable of suppressing the enzymatic conversion of sugar macromolecules into their smaller units. Herein, we reported the discovery of a series of substituted triazolo[4,3‐b][1,2,4]triazine derivatives as α‐glucosidase and α‐amylase inhibitors. All target compounds demonstrated significant inhibitory activities against α‐glucosidase and α‐amylase enzymes compared with acarbose as the positive control. The most potent compound 10k, 2‐[(6‐phenyl‐[1,2,4]triazolo[4,3‐b][1,2,4]triazin‐3‐yl)thio]‐N‐[4‐(trifluoromethyl)phenyl]acetamide, demonstrated IC₅₀ values of 31.87 and 24.64 nM against α‐glucosidase and α‐amylase enzymes, respectively. To study their mechanism of action, kinetic studies were also done, which determined the mode of inhibition of both enzymes. Molecular docking was used to confirm the binding interactions of the most active compounds.

  DOI：

  10.1002/ardp.202300628

文献信息

• Dehuri, S. N.; Pradhan, P. C.; Nayak, A., Journal of the Indian Chemical Society, 1983, vol. 60, p. 475 - 478
  作者：Dehuri, S. N.、Pradhan, P. C.、Nayak, A.

  DOI：——

  日期：——
• ——
  作者：Yu. Yu. Morzherin、T. A. Pospelova、T. V. Glukhareva、V. S. Berseneva、Yu. A. Rozin、E. V. Tarasov、V. A. Bakulev

  DOI：10.1023/a:1013861930028

  日期：——
• DEHURI, S. N.;PRADHAN, P. C.;NAYAK, A., J. INDIAN CHEM. SOC., 1983, 60, N 5, 475-478
  作者：DEHURI, S. N.、PRADHAN, P. C.、NAYAK, A.

  DOI：——

  日期：——
• Synthesis, biological activities, and molecular docking studies of triazolo[4,3‐<i>b</i>]triazine derivatives as a novel class of α‐glucosidase and α‐amylase inhibitors
  作者：Soheila Seyfi、Somayeh Salarinejad、Setareh Moghimi、Mahsa Toolabi、Nastaran Sadeghian、Burak Tüzün、Loghman Firoozpour、Shima H. M. E. Ketabforoosh、Parham Taslimi、Alireza Foroumadi

  DOI：10.1002/ardp.202300628

  日期：——

  In diabetes mellitus, amylase and glucosidase enzymes are the primary triggers. The main function of these enzymes is to break macromolecules into simple sugar units, which directly affect blood sugar levels by increasing blood permeability. To overcome this metabolic effect, there is a need for a potent and effective inhibitor capable of suppressing the enzymatic conversion of sugar macromolecules into their smaller units. Herein, we reported the discovery of a series of substituted triazolo[4,3‐b][1,2,4]triazine derivatives as α‐glucosidase and α‐amylase inhibitors. All target compounds demonstrated significant inhibitory activities against α‐glucosidase and α‐amylase enzymes compared with acarbose as the positive control. The most potent compound 10k, 2‐[(6‐phenyl‐[1,2,4]triazolo[4,3‐b][1,2,4]triazin‐3‐yl)thio]‐N‐[4‐(trifluoromethyl)phenyl]acetamide, demonstrated IC₅₀ values of 31.87 and 24.64 nM against α‐glucosidase and α‐amylase enzymes, respectively. To study their mechanism of action, kinetic studies were also done, which determined the mode of inhibition of both enzymes. Molecular docking was used to confirm the binding interactions of the most active compounds.