3-[2-(2-{2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-ylcarbamoyl}-1-methylimidazol-4-ylcarbamoyl)-1-methylimidazol-4-yl]-3,4-dihydro-3-methyl-4-oxoimdazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑四嗪类
• 英文名称: 3-[2-(2-{2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-ylcarbamoyl}-1-methylimidazol-4-ylcarbamoyl)-1-methylimidazol-4-yl]-3,4-dihydro-3-methyl-4-oxoimdazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
• 英文别名: N-[2-[[2-[[2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]carbamoyl]-1-methylimidazol-4-yl]-3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
• 化学式: C₂₅H₃₀N₁₆O₅
• 分子量: 634.617
• InChiKey: CUUJYKYQCGGBIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  236
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  替莫唑胺 在 氯化亚砜 、 硫酸 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-[2-(2-{2-[2-(dimethylamino)ethylcarbamoyl]-1-methylimidazol-4-ylcarbamoyl}-1-methylimidazol-4-ylcarbamoyl)-1-methylimidazol-4-yl]-3,4-dihydro-3-methyl-4-oxoimdazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
  参考文献：
  名称：

  Antitumor Imidazotetrazines. 41. Conjugation of the Antitumor Agents Mitozolomide and Temozolomide to Peptides and Lexitropsins Bearing DNA Major and Minor Groove-Binding Structural Motifs

  摘要：

  Carboxylic acids derived from the amido groups of the antitumor agents mitozolomide and temozolomide have been conjugated to simple amino acids and peptides by carbodiimide coupling. Solid-state peptide synthesis has been applied to link the acids to DNA major groove-binding peptidic motifs known to adopt alpha-helical conformations. Attachment of the acids to pyrrole and imidazole polyamidic lexitropsins gave a series of potential DNA minor groove- binding ligands. In vitro biological evaluation of a limited number of these novel conjugates failed to demonstrate any enhanced growth-inhibitory activity compared to the unconjugated drugs; sites of alkylation at tracts of multiple guanines were also unaffected. Attachment of additional residues at C-8 of the imidazotetrazines did not perturb the chemistry of activation of the bicyclic nucleus, and biological sequelae can be rationalized by invoking the liberation of a common, diffusible, reactive chemical intermediate, the methanediazonium ion.

  DOI：

  10.1021/jm020936d