6-[(4-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid | 52128-06-0

• 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: 6-[(4-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid
• CAS: 52128-06-0
• 化学式: C₂H₄O₂*C₁₅H₁₄ClN₅
• 分子量: 359.815
• InChiKey: KVBBZHJCRZWEOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  127.15
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  对氯苯胺 、 溶剂黄146 、 2,4-diamino-6-quinazoline-6-carbonitrile 在 镍 氢气 作用下， 28.0 ℃ 、344.73 kPa 条件下， 反应 22.0h， 以47%的产率得到6-[(4-Chloro-phenylamino)-methyl]-quinazoline-2,4-diamine; compound with acetic acid
  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