2,4-diglycidyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione | 80150-69-2

• 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: 2,4-diglycidyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione
• 英文别名: 1,3-bis(2,3-epoxypropyl)-6-azauracil；2,4-bis(oxiran-2-ylmethyl)-1,2,4-triazine-3,5-dione
• CAS: 80150-69-2
• 化学式: C₉H₁₁N₃O₄
• 分子量: 225.204
• InChiKey: GBSPEKSTQQRLMO-UHFFFAOYSA-N

物化性质

• 沸点：
  362.2±38.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异丙胺 、 2,4-diglycidyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione 以 水 为溶剂， 以70%的产率得到1,3-bis(2-hydroxy-3-isopropylaminopropyl)-6-azauracil
  参考文献：
  名称：

  Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties

  摘要：

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80090-7
• 作为产物：
  描述：

  6-氮杂脲嘧啶 、 环氧氯丙烷 在 四乙基溴化铵 、 氢氧化钾 作用下， 以 乙二醇二甲醚 为溶剂， 以36%的产率得到2,4-diglycidyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties

  摘要：

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80090-7

文献信息

• Arzneimittel mit cytostatischer Wirkung sowie Verwendung von mehrfach mit Glycidylgruppen substituierten N-heterocyclischen Ringverbindungen in pharmazeutischen Zubereitungen
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0033503A2

  公开（公告）日：1981-08-12

  Geschildert werden Arzneimittelzubereitungen mit cytostatischer Wirksamkeit, die gekennzeichnet sind durch einen Gehalt an N-Heterocyclen, die wenigstens zwei Glycidyl-substituierte N-Atome in Amid- und/oder Imidform in das Ringsystem eingebunden enthalten. Der Glycidylrest entspricht dabei der Formel wobei R Wasserstoff oder ein Alkylrest mit 1 bis 4 C-Atomen ist. Bevorzugt bedeutet R Wasserstoff. Triglycidylisocyanurat und Diglycidylisocyanurat, die am dritten Ringstickstoff ) gegebenenfalls substituierte Kohlenwasserstoffreste aufweisen, und deren Verwendung in entsprechenden Arzneimittel- ) zubereitungen Gegenstand älterer Anmeldungen ist, werden hier nicht beansprucht.

  本文描述了具有细胞抑制活性的药物制剂，其特点是含有至少两个缩水甘油基取代的 N 原子，这些 N 原子以酰胺和/或亚胺形式结合到环系统中。缩水甘油残基符合以下式子 其中 R 为氢或具有 1 至 4 个碳原子的烷基。R 最好是氢。异氰尿酸三缩水甘油酯和异氰尿酸二缩水甘油酯在第三环氮上有任选取代的烃基，其在相应药物制剂中的应用是旧申请的主题，在此不作要求。
• Fischer; Moller; Budnowski, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 6, p. 663 - 668
  作者：Fischer、Moller、Budnowski、et al.

  DOI：——

  日期：——
• Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties
  作者：Silvana Raić-Malić、Mira Grdiša、Krešimir Pavelic、Mladen Mintas

  DOI：10.1016/s0223-5234(99)80090-7

  日期：1999.5

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.