2-benzyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7(4H,6H)-dione | 1431968-83-0

• 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: 2-benzyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7(4H,6H)-dione
• 英文别名: 2-benzyl-4H-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-dione
• CAS: 1431968-83-0
• 化学式: C₁₁H₉N₅O₂
• 分子量: 243.225
• InChiKey: PCYOLXSEEPZFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  88.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-Phenylacetyl-N'-guanyl-hydrazin 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.33h， 生成 2-benzyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7(4H,6H)-dione
  参考文献：
  名称：

  A structure–activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities

  摘要：

  Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the 5-thioxo analogues of 1,2,4-triazolo[1,5-a][1,3,5]triazine exhibited a varying degree of inhibitory activity towards thymidine phosphorylase, comparable or better than reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). Moreover, compounds 5q and 6i displayed a mixed-type of inhibitory mechanism in the presence of variable concentrations of thymidine (dThd). In addition, selected compounds were found to have a noticeable inhibitory effect on the expression of angiogenesis markers, including VEGF and MMP-9 in MDA-MB-231 breast cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.051

文献信息

• Synthesis, in vitro evaluation of thymidine phosphorylase inhibitory activity, and in silico study of 1,3,5-triazin-2,4-dione and its fused analogues
  作者：Hriday Bera、Wai-Keung Chui、Sayan Dutta Gupta、Anton V. Dolzhenko、Lingyi Sun

  DOI：10.1007/s00044-013-0589-1

  日期：2013.12

  5-triazin-2,4-dione and their fused analogues was designed, synthesized and their in vitro thymidine phosphorylase inhibitory potential was evaluated. The monocyclic analogues were found to be inactive. Among the different fused derivatives synthesized, compounds having keto group (C=O) at C7/C4 and thioketo group (C=S) at C5/C2 position showed TP inhibitory activity comparable to positive control, 7-deazaxanthine

  基于与参考化合物的结构相似性，设计，合成了一系列1,3,5-triazin-2,4-dione及其融合类似物，并对其体外胸苷磷酸化酶抑制潜力进行了评估。发现单环类似物是无活性的。在合成的不同稠合衍生物中，在C7 / C4处具有酮基（C = O）和在C5 / C2位置具有硫酮基（C = S）的化合物显示出与阳性对照7-脱氮黄嘌呤（7-DX）相当的TP抑制活性。（IC 50值= 42.63μM）。进行了目标化合物与胸苷磷酸化酶的分子对接，以说明关于合理的配体-酶结合相互作用的重要结构信息。