5-cyclopentyl-7-((4-(cyclopentylamino)phenyl)amino)-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 5-cyclopentyl-7-((4-(cyclopentylamino)phenyl)amino)-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one
• 英文别名: 5-Cyclopentyl-7-[4-(cyclopentylamino)anilino]-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4-one；5-cyclopentyl-7-[4-(cyclopentylamino)anilino]-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4-one
• 化学式: C₂₄H₂₈N₈O
• 分子量: 444.539
• InChiKey: BASZPCNKZLXFIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2-氯-5-硝基-嘧啶-4-基)-环戊基-胺 在 盐酸 、 氯化亚砜 、 铁粉 、 potassium carbonate 、 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 正丁醇 为溶剂， 反应 25.0h， 生成 5-cyclopentyl-7-((4-(cyclopentylamino)phenyl)amino)-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivative as potent antitumor agents

  摘要：

  To develop novel therapeutic agents with anticancer activities, two series of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivatives were designed and synthesized. All compounds were tested for anti-proliferative activities against five cancer cell lines. The structure-activity relationships (SARs) studies were conducted through the variation in two regions, the moiety of A ring and the terminal aniline B on pteridinone core. 1-Methyl-1,2,4-triazole derivative L-7 with 2,6-dimethylpiperazine showed the most potent antiproliferative activity against A549, PC-3, HCT116, MCF-7 and MDA-MB-231 cell lines with IC50 values of 0.16 mu M, 0.30 mu M, 0.511 mu M, 0.30 mu M, and 0.70 mu M, respectively. Combined with the results of the molecular docking and enzymatic studies, the PLK1 was very likely to be one of the drug targets of compound L7. Furthermore, to clarify the anticancer mechanism of compound L7, further explorations in the bioactivity were conducted. The results showed that compound L7 obviously inhibited proliferation of A549 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells, and arrested G1 phase of A549 cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.009