N²-p-tolyl-9-β-D-ribofuranosylguanine | 77976-95-5

• 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-p-tolyl-9-β-D-ribofuranosylguanine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(4-methylanilino)-3H-purin-6-one
• CAS: 77976-95-5
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: PFAJSGBHQNJPFQ-XNIJJKJLSA-N

物化性质

• 熔点：
  244-246 °C
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  145.52
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N²-p-tolyl-9-β-D-ribofuranosylguanine 在 磷酸三甲酯 、 三丁基焦磷酸铵 、 N,N'-羰基二咪唑 、 三氯氧磷 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 14.0h， 生成 N²-p-tolyl-9-β-D-ribofuranosylguanine 5'-triphosphate
  参考文献：
  名称：

  Interaction of GTP derivatives with cellular and oncogenic ras-p21 proteins

  摘要：

  A series of N2-substituted guanosine 5'-triphosphates was synthesized from the corresponding nucleosides. The nucleosides were prepared by treatment of N2-substituted guanines with tetra-O-acetylribose under conditions which maximized the yield of the 9-beta-guanosine isomers. These nucleotides and several sugar- and base-modified analogues of GTP were tested for their ability to bind to cellular and oncogenic forms of the GTP/GDP binding proteins, Ha-ras-p21. Several N2-substituted GTPs showed affinities higher than that of GDP itself, and the N2-[p-(n-butyl)phenyl] derivative bound to the oncogenic mutant, Leu-61 p21, twice as strongly as to the cellular protein. Changes in relative affinities of the nucleotides are discussed with reference to reported crystallographic structures of p21.

  DOI：

  10.1021/jm00108a010
• 作为产物：
  描述：

  9-((triacetyl)-β-D-ribofuranosyl)-N2-(p-tolyl)guanosine 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

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：——