3-(2-chloroethyl)-8-diazoacetylimidazo<5,1-d>-1,2,3,5-tetrazin-4(3H)-one | 113942-40-8

• 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-chloroethyl)-8-diazoacetylimidazo<5,1-d>-1,2,3,5-tetrazin-4(3H)-one
• 英文别名: 3-(2-Chloroethyl)-8-(2-diazoacetyl)imidazo[5,1-d][1,2,3,5]tetrazin-4-one
• CAS: 113942-40-8
• 化学式: C₈H₆ClN₇O₂
• 分子量: 267.634
• InChiKey: QWCLPWXSOOKEJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-氯乙基)-4-氧代-3H-咪唑并(5,1-d)-1,2,3,5-四嗪-8-羧酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 3-(2-chloroethyl)-8-diazoacetylimidazo<5,1-d>-1,2,3,5-tetrazin-4(3H)-one
  参考文献：
  名称：

  Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents

  摘要：

  The preparation of 3-(2-chlorethyl)-4-oxo-3H-imidazo[5,1-d]-1,2,3,5- tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described. The facile conversion to the 8-carbonyl chloride gave a derivative that reacted preferentially with nucleophiles at the 8-position rather than at the reactive 4-oxo group, allowing the preparation of a wide range of ester, thioester, amide (including an amide derived from an amino acid), hydroxamic acid, hydrazide and sulfoximide, azide and diazoacetyl derivatives. The in vivo activity is presented of a range of these compounds against TLX5 lymphoma and L1210 leukemia cell lines.

  DOI：

  10.1021/jm00167a018