8-[2-[(2-Hydroxyphenyl)methylidene]hydrazinyl]-1,3,7-trimethylpurine-2,6-dione | 6306-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-[2-[(2-Hydroxyphenyl)methylidene]hydrazinyl]-1,3,7-trimethylpurine-2,6-dione
• CAS: 6306-69-0
• 化学式: C₁₅H₁₆N₆O₃
• mdl: MFCD00497745
• 分子量: 328.33
• InChiKey: ITVKVMVWIJENNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  咖啡因 在 氯 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 75.0h， 生成 8-[2-[(2-Hydroxyphenyl)methylidene]hydrazinyl]-1,3,7-trimethylpurine-2,6-dione
  参考文献：
  名称：

  Caffeine–hydrazones as anticancer agents with pronounced selectivity toward T-lymphoblastic leukaemia cells

  摘要：

  We report design and synthesis of set of novel anticancer agents based on caffeine-hydrazones bearing 2-hydroxyaryl- or 2-N-heteroaryl moiety. Anticancer activity evaluation using seven cancer cell lines and two non-malignant cell lines demonstrated that several derivatives display significant anticancer activity and great selectivity index toward T-lymphoblastic leukaemia cells. In general, hydrazones bearing 2-N-heteroaryl moiety are more active and selective than those with 2-hydroxyaryl moiety. Tested compounds exhibit dose-dependent inhibition of both RNA and DNA synthesis, with some exceptions. Antimicrobial activities were tested on set of twelve bacterial and yeast strains, however prepared compounds were not active, suggesting for a molecular target specific for eukaryotic cells. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.03.003

文献信息

• Caffeine–hydrazones as anticancer agents with pronounced selectivity toward T-lymphoblastic leukaemia cells
  作者：Robert Kaplánek、Milan Jakubek、Jakub Rak、Zdeněk Kejík、Martin Havlík、Bohumil Dolenský、Ivo Frydrych、Marián Hajdúch、Milan Kolář、Kateřina Bogdanová、Jarmila Králová、Petr Džubák、Vladimír Král

  DOI：10.1016/j.bioorg.2015.03.003

  日期：2015.6

  We report design and synthesis of set of novel anticancer agents based on caffeine-hydrazones bearing 2-hydroxyaryl- or 2-N-heteroaryl moiety. Anticancer activity evaluation using seven cancer cell lines and two non-malignant cell lines demonstrated that several derivatives display significant anticancer activity and great selectivity index toward T-lymphoblastic leukaemia cells. In general, hydrazones bearing 2-N-heteroaryl moiety are more active and selective than those with 2-hydroxyaryl moiety. Tested compounds exhibit dose-dependent inhibition of both RNA and DNA synthesis, with some exceptions. Antimicrobial activities were tested on set of twelve bacterial and yeast strains, however prepared compounds were not active, suggesting for a molecular target specific for eukaryotic cells. (C) 2015 Elsevier Inc. All rights reserved.