2-phenyl-7-thioxo-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-one | 40597-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-7-thioxo-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-one
• 英文别名: 2-phenyl-7-thioxo-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-one
• CAS: 40597-80-6
• 化学式: C₁₀H₇N₅OS
• 分子量: 245.264
• InChiKey: XBNVTSLMUMSWOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.84
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-7-thioxo-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-one 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 生成 2-phenyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5,7(4H,6H)-dione
  参考文献：
  名称：

  Synthesis andin vitroEvaluation of 1,2,4-Triazolo[1,5-a][1,3,5]triazine Derivatives as Thymidine Phosphorylase Inhibitors

  摘要：

  In our lead finding program, a series of 1,2,4‐triazolo[1,5‐a][1,3,5]triazine derivatives were synthesized, and their in vitro thymidine phosphorylase inhibitory potential was explored. Among the different derivatives, compounds having keto group (C = O) at C7 and thioketo group (C = S) at C5 positions showed varying degrees of TP inhibitory activity comparable with positive control, 7‐deazaxanthine (7‐DX, 2) (IC50 value = 42.63 μm). Enzyme inhibition kinetics study suggested that compound IVn behaved as a mixed‐type inhibitor of the enzyme with respect to thymidine (dThd) as a variable substrate. Compound IVn was also found to inhibit PMA‐induced MMP‐9 expression in MDA‐MB‐231 cells at sublethal concentrations. Computational docking study was performed to illustrate the enzyme inhibition kinetics and to explore the ligand–enzyme interactions.

  DOI：

  10.1111/cbdd.12171
• 作为产物：
  描述：

  3-氨基-5-苯基-1,2,4-三唑 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 0.66h， 生成 2-phenyl-7-thioxo-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-one
  参考文献：
  名称：

  Synthesis andin vitroEvaluation of 1,2,4-Triazolo[1,5-a][1,3,5]triazine Derivatives as Thymidine Phosphorylase Inhibitors

  摘要：

  In our lead finding program, a series of 1,2,4‐triazolo[1,5‐a][1,3,5]triazine derivatives were synthesized, and their in vitro thymidine phosphorylase inhibitory potential was explored. Among the different derivatives, compounds having keto group (C = O) at C7 and thioketo group (C = S) at C5 positions showed varying degrees of TP inhibitory activity comparable with positive control, 7‐deazaxanthine (7‐DX, 2) (IC50 value = 42.63 μm). Enzyme inhibition kinetics study suggested that compound IVn behaved as a mixed‐type inhibitor of the enzyme with respect to thymidine (dThd) as a variable substrate. Compound IVn was also found to inhibit PMA‐induced MMP‐9 expression in MDA‐MB‐231 cells at sublethal concentrations. Computational docking study was performed to illustrate the enzyme inhibition kinetics and to explore the ligand–enzyme interactions.

  DOI：

  10.1111/cbdd.12171

文献信息

• Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines
  作者：Junaid、Lim、Zhou、Chui、Dolzhenko

  DOI：10.3390/molecules24081453

  日期：——

  demonstrated. The most practical and general method for the preparation of 5-aza-isoguanines involved a regioselective reaction of ethoxycarbonyl isothiocyanate with a 5-aminotriazole. The intramolecular ring closure of the resulted product followed by the S-methylation afforded 7-methylthio-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, which could be effectively aminated with various amines. The resulted

  嘌呤等排体在药物设计和开发中提供了极好的机会。使用天然嘌呤的等排体作为构建新治疗剂的支架已成为药物化学的有效策略。受到与异鸟嘌呤的相似性的启发，我们尝试开发一种实用的方法来制备 5-氮杂-异鸟嘌呤。探索了几种合成方法，以建立用于制备这些化合物的稳健通用方案。证明了 1,2,4-三唑并[1,5-a][1,3,5]三嗪（5-氮杂嘌呤）的 C-5 和 C-7 亲电中心对亲核试剂的反应性存在显着差异。制备 5-氮杂-异鸟嘌呤的最实用和通用的方法涉及乙氧羰基异硫氰酸酯与 5-氨基三唑的区域选择性反应。所得产物的分子内闭环，然后进行 S-甲基化，得到 7-甲硫基-2-苯基-1,2,4-三唑并[1,5-a][1,3,5]triazin-5-one，可与各种胺有效胺化。由此产生的 5-氮杂-异鸟嘌呤类似于一种已知的嘌呤核苷磷酸化酶抑制剂，对于作为潜在抗癌剂的进一步研究可能很有趣。