N-[(2,4-diamino-5-methylquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)nitrous amide | 52128-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[(2,4-diamino-5-methylquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)nitrous amide
• CAS: 52128-38-8
• 化学式: C₁₆H₁₄Cl₂N₆O
• 分子量: 377.233
• InChiKey: XWUYLZPZGCTEFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-<<(3,4-dichlorophenyl)amino>methyl>-5-methyl-2,4-quiazolinediamine acetate 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以31%的产率得到N-[(2,4-diamino-5-methylquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)nitrous amide
  参考文献：
  名称：

  Folate antagonists. 20. Synthesis and antitumor and antimalarial properties of trimetrexate and related 6-[(phenylamino)methyl]-2,4-quinazolinediamines

  摘要：

  A series of 6-[(arylamino)methyl]-2,4-quinazolinediamines have been prepared by catalytic hydrogenation of the requisite 2,4-diamino-6-quinazolinecarbonitriles in the presence of the appropriate benzenamine. Formylation, acetylation, and nitrosation provided N omega derivatives of these compounds. A variety of the compounds exhibited potent antimalarial, antibacterial, and antitumor activity. In particular, 5-methyl-6-[[(3,4,5-trimethoxyphenyl)-amino]methyl]-2, 4-quinazolinediamine (trimetrexate, 15) has shown a broad spectrum of antitumor effects and is undergoing preclinical toxicology evaluation prior to trial in man.

  DOI：

  10.1021/jm00366a018