2,4-二氨基-5-氯-6-[(3,4-二氯苯胺基)甲基]喹唑啉单乙酸酯 | 52128-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2,4-二氨基-5-氯-6-[(3,4-二氯苯胺基)甲基]喹唑啉单乙酸酯
• 英文名称: 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline monoacetate
• 英文别名: Acetic acid;5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline-2,4-diamine
• CAS: 52128-44-6
• 化学式: C₂H₄O₂*C₁₅H₁₂Cl₃N₅
• 分子量: 428.705
• InChiKey: FXVNLDJOPDKQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  27
• 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：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-二氨基-5-氯-6-[(3,4-二氯苯胺基)甲基]喹唑啉单乙酸酯 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75%的产率得到N-[(2,4-diamino-5-chloroquinazolin-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
• 作为产物：
  描述：

  溶剂黄146 、 3,4-二氯苯胺 、 2,4-diamino-5-chloroquinazoline-6-carbonitrile 在 镍 氢气 作用下， 28.0 ℃ 、344.73 kPa 条件下， 反应 22.0h， 以29%的产率得到2,4-二氨基-5-氯-6-[(3,4-二氯苯胺基)甲基]喹唑啉单乙酸酯
  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

文献信息

• US4391809A
  申请人：——

  公开号：US4391809A

  公开（公告）日：1983-07-05
• Folate antagonists. 20. Synthesis and antitumor and antimalarial properties of trimetrexate and related 6-[(phenylamino)methyl]-2,4-quinazolinediamines
  作者：Edward F. Elslager、Judith L. Johnson、Leslie M. Werbel

  DOI：10.1021/jm00366a018

  日期：1983.12

  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.