N²-phenyl-9-(2-deoxy-β-D-ribofuranosyl)guanine | 114300-71-9

• 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: N²-phenyl-9-(2-deoxy-β-D-ribofuranosyl)guanine
• 英文别名: N²-phenyl-2'-deoxyguanosine；N²-phenyldeoxyguanosine；n2-Phenyldeoxyguanosine；2-anilino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 114300-71-9
• 化学式: C₁₆H₁₇N₅O₄
• 分子量: 343.342
• InChiKey: WGYVNLWYYLACQQ-QJPTWQEYSA-N

物化性质

• 熔点：
  128-131 °C
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴次黄嘌呤 在 氯化亚砜 、 sodium methylate 、 sodium hydride 、 2-巯基乙醇 作用下， 以 甲醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 77.83h， 生成 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

文献信息

• Chemoselective arylation of 2′-deoxyguanosine at N-2 with organoiron complexes
  作者：Gerard A. Potter、Raymond McCague、Michael Jarman

  DOI：10.1039/c39920000637

  日期：——

  2′-Deoxyguanosine has been directly and chemoselectively arylated at the N2-amino function by treatment with tricarbonyl(η5-cyclohexadienylium)iron or tricarbonyl[η5-2-(n-butyl)cyclohexadienylium]iron cations, followed by decomplexation and dehydrogenation, providing a rapid route to N2-aryl-2′-deoxyguanosine nucleosides.

  通过使用三羰基（δ-5-环己二烯基）铁或三羰基[δ-5-2-（正丁基）环己二烯基]铁阳离子处理 2'²-脱氧鸟苷，然后进行脱氨化和脱氢反应，可直接并化学选择性地在 N2-氨基功能处芳基化，从而为 N2-芳基-2'²-脱氧鸟苷核苷提供了一条快速途径。
• 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：——
• N2-Phenyldeoxyguanosine: a novel selective inhibitor of herpes simplex thymiding kinase
  作者：Federico Focher、Catherine Hildebrand、Stephen Freese、Giovanni Ciarrocchi、Timothy Noonan、Stefano Sangalli、Neal Brown、Silvio Spadari、George Wright

  DOI：10.1021/jm00403a004

  日期：1988.8

  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.