N2-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine | 158729-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N2-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine
• 英文别名: N²-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine
• CAS: 158729-54-5
• 化学式: C₂₀H₂₃N₅O₃
• 分子量: 381.434
• InChiKey: PROBIZIEPAYBSK-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.2
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N2-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以81%的产率得到N²-(4-n-Butylphenyl)-3'-acetyl-2'deoxy-3,5'-cycloguanosine
  参考文献：
  名称：

  Amino-Imino Tautomerization of N2-(4-n-Butylphenyl)-2'-deoxy-3,5'-cycloguanosine

  摘要：

  N-2-(4-n-Butylphenyl)-2'- deoxy-3,5'-cycloguanosine (cBuPdG) has been studied by one-dimensional 1H and 13C, two-dimensional TOCSY, HMQC, and HMBC, and long range selective INEPT NMR experiments. In DMF and DMSO solutions cBuPdG exists asa mixture of two isomers involved in a slow rate of interconversion which have been identified as N-2 amino-imino tautomers, while in chloroform only the imino tautomer is present. It has been proved that the tautomeric form of the parent nucleoside, N-2-(4-n-butylphenyl)-2'-deoxyguanosine (BuPdG), is N-2 amino. The selective INEPT experiment can be used efficiently in assignment of tautomeric structures of nucleosides.

  DOI：

  10.1021/jo00101a037
• 作为产物：
  描述：

  N-(4-丁基苯基)-2'-脱氧鸟苷 在 吡啶 、 四丁基氢氧化铵 作用下， 反应 0.5h， 生成 N2-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine
  参考文献：
  名称：

  Synthesis of the P¹, P²-Methylene Analog of N²- (p-n-Butylphenyl)-2′- deoxyguanosine 5′-Triphosphate: A Non-substrate Inhibitor of DNA Polymerases

  摘要：

  N-2-(p-n-Butylphenyl)-2'-deoxyguanosine 5'-(P-1,P-2-methylene)-triphosphate (BuPdGMPCH(2)PP) has been synthesized. Displacement of the mesyloxy group of 5'-MesBuPdG by methanediphosphonate gave 30% of BuPdGMPCH(2)P, but 68% of 3,5'-cycloBuPdG. Reaction of the nucleoside BuPdG with methanediphosphonate and DCC gave 62% of BuPdGMPCH(2)PPCH(2)P, which was hydrolyzed to BuPdGMPCH(2)P in 77% yield. The title compound was obtained by reacting the imidazolide of BuPdGMPCH(2)P with orthophosphate. BuPdGMPCH(2)PP inhibited calf thymus DNA polymerase a with K-i = 9.5 nM, a potency only fivefold weaker than that of BuPdGTP itself.

  DOI：

  10.1080/15257779408013245