2-(4-甲基苯胺基)-3,7-二氢嘌呤-6-酮 | 57338-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(4-甲基苯胺基)-3,7-二氢嘌呤-6-酮
• 英文名称: 2-p-tolylamino-1,7(9)-dihydro-purin-6-one
• 英文别名: 6H-Purin-6-one, 1,9-dihydro-2-[(4-methylphenyl)amino]-；2-(4-methylanilino)-1,7-dihydropurin-6-one
• CAS: 57338-66-6
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: HFXAMEWMAYIKHR-UHFFFAOYSA-N

物化性质

• 熔点：
  332-335 °C
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯胺基)-3,7-二氢嘌呤-6-酮 在 氨 作用下， 以 甲醇 为溶剂， 生成 N²-p-tolyl-9-β-D-ribofuranosylguanine
  参考文献：
  名称：

  N2-Phenyldeoxyguanosine: a novel selective inhibitor of herpes simplex thymiding kinase

  摘要：

  A series of N2-substituted guanine derivatives was screened against mammalian thymidine kinase and the thymidine kinase encoded by type I herpes simplex virus to examine their capacity to selectivity inhibit the viral enzyme. Several bases, nucleosides, and nucleotides displayed selective activity. The mechanism of action of the most potent derivative, N2-phenyl-2'-deoxyguanosine (PhdG) was studied in detail. PhdG (a) inhibited the viral enzyme competitively with respect to the substrates thymidine and deoxycytidine, (b) was completely resistant to phosphorylation, (c) displayed limited toxicity for the HeLa cell lines employed as hosts for viral infection, and (d) selectively inhibited viral thymidine kinase function in intact cultured cells. The results indicate that the PhdG drug prototype has potential as a selective anti-herpes agent and as a novel molecular probe of the structure and function of herpes simplex thymidine kinase.

  DOI：

  10.1021/jm00403a004
• 作为产物：
  描述：

  2-溴次黄嘌呤 、 乙烷,三氯氟- 以 乙二醇甲醚 为溶剂， 以69%的产率得到2-(4-甲基苯胺基)-3,7-二氢嘌呤-6-酮
  参考文献：
  名称：

  N2-Phenyldeoxyguanosine: a novel selective inhibitor of herpes simplex thymiding kinase

  摘要：

  A series of N2-substituted guanine derivatives was screened against mammalian thymidine kinase and the thymidine kinase encoded by type I herpes simplex virus to examine their capacity to selectivity inhibit the viral enzyme. Several bases, nucleosides, and nucleotides displayed selective activity. The mechanism of action of the most potent derivative, N2-phenyl-2'-deoxyguanosine (PhdG) was studied in detail. PhdG (a) inhibited the viral enzyme competitively with respect to the substrates thymidine and deoxycytidine, (b) was completely resistant to phosphorylation, (c) displayed limited toxicity for the HeLa cell lines employed as hosts for viral infection, and (d) selectively inhibited viral thymidine kinase function in intact cultured cells. The results indicate that the PhdG drug prototype has potential as a selective anti-herpes agent and as a novel molecular probe of the structure and function of herpes simplex thymidine kinase.

  DOI：

  10.1021/jm00403a004

文献信息

• FOCHER, FEDERICO;HILDEBRAND, CATHERINE;FREESE, STEPHEN;CIARROCCHI, GIOVAN+, J. MED. CHEM., 31,(1988) N 8, C. 1496-1500
  作者：FOCHER, FEDERICO、HILDEBRAND, CATHERINE、FREESE, STEPHEN、CIARROCCHI, GIOVAN+

  DOI：——

  日期：——