2-anilino-6-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine | 114300-78-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-anilino-6-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine
• CAS: 114300-78-6
• 化学式: C₁₆H₁₆ClN₅O₃
• 分子量: 361.788
• InChiKey: QQKAMIXYEHKSKX-QJPTWQEYSA-N

物化性质

• 沸点：
  680.6±65.0 °C(predicted)
• 密度：
  1.67±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105.32
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-anilino-6-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine 在 sodium methylate 、 2-巯基乙醇 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以62%的产率得到N²-phenyl-9-(2-deoxy-β-D-ribofuranosyl)guanine
  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：

  6-chloro-N-phenyl-9H-purin-2-amine 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.83h， 生成 2-anilino-6-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine
  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