N⁶-<(3,4-dichlorophenyl)methyl>-N⁶-methyl-2,4,6-pteridinetriamine | 76532-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: N⁶-<(3,4-dichlorophenyl)methyl>-N⁶-methyl-2,4,6-pteridinetriamine
• 英文别名: N⁶-[(3,4-dichlorophenyl)methyl]-N⁶-methyl-2,4,6-pteridinetriamine；6-N-[(3,4-dichlorophenyl)methyl]-6-N-methylpteridine-2,4,6-triamine
• CAS: 76532-16-6
• 化学式: C₁₄H₁₃Cl₂N₇
• 分子量: 350.21
• InChiKey: JCKOETYVOVTWAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  303-305 °C(Solv: acetic acid (64-19-7); water (7732-18-5))
• 沸点：
  639.0±65.0 °C(Predicted)
• 密度：
  1.566±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-二氯苯甲醛 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 N⁶-<(3,4-dichlorophenyl)methyl>-N⁶-methyl-2,4,6-pteridinetriamine
  参考文献：
  名称：

  Folate antagonists. 18. Synthesis and antimalarial effects of N6-(arylmethyl)-N6-methyl-2,4,6-pteridinetriamines and related N6,N6-disubstituted 2,4,6-pteridinetriamines

  摘要：

  N6-(Arylmethyl)-N6-methyl-2,4,6-pteridinetriamines (1-15) and related N6-substituted 2,4,6-pteridinetriamines (16-20) were obtained by the condensation of 6-chloro-2,4-pteridinediamine with N-methylarylmethanamine and other selected secondary amines. The requisite N-methylarylmethanamines (21-32) were prepared by the hydrogenation over Pt/C of the corresponding arylcarboxaldehyde in the presence of methanamine. Several of the N6-(arylmethyl)-N6-methyl-2,4,6-pteridinetriamines exhibited exceptional suppressive antimalarial activity against a drug-sensitive line of Plasmodium berghei in mice. N6-Methyl-N6-(1-naphthalenylmethyl)-2,4,6-pteridinetriamine (9), the most active of these compounds, was also shown to be curative at 3.16 mg/kg in a single oral dose against P. cynomolgi in the rhesus monkey. This compound was also shown to be effective against a chloroquine-resistant line of P. berghei in the mouse but showed cross-resistance to a pyrimethamine-resistant strain. Most of the 2,4,6-pteridinetriamines showed strong antibacterial action against Streptococcus faecalis and Staphylococcus aureus.

  DOI：

  10.1021/jm00134a003

文献信息

• ELSLAGER E. F.; JOHNSON J. L.; WERBEL L. M., J. MED. CHEM., 1981, 24, NO 2, 140-145
  作者：ELSLAGER E. F.、 JOHNSON J. L.、 WERBEL L. M.

  DOI：——

  日期：——