N²-(p-n-butylphenyl)-2'-deoxyguanosine 5'-(P¹,P²-methylene)triphosphate

• 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-(p-n-butylphenyl)-2'-deoxyguanosine 5'-(P¹,P²-methylene)triphosphate
• 英文别名: [(2R,3S,5R)-5-[2-(4-butylanilino)-6-oxo-1H-purin-9-yl]-3-hydroxyoxolan-2-yl]methoxy-[[hydroxy(phosphonooxy)phosphoryl]methyl]phosphinic acid
• 化学式: C₂₁H₃₀N₅O₁₂P₃
• 分子量: 637.417
• InChiKey: DKIXNKYJUQCDMV-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  251
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  ({(2R,3S,5R)-5-[2-(4-Butyl-phenylamino)-6-oxo-1,6-dihydro-purin-9-yl]-3-hydroxy-tetrahydro-furan-2-ylmethoxy}-hydroxy-phosphorylmethyl)-phosphonic acid; compound with triethyl-amine 在 六甲基磷酰三胺 、 三正丁胺 、 Dowex 50 、 N,N-二丁基丁烷-1-胺,磷酸 、 N,N'-羰基二咪唑 作用下， 生成 N²-(p-n-butylphenyl)-2'-deoxyguanosine 5'-(P¹,P²-methylene)triphosphate
  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

文献信息

• Synthesis of the P¹, P²-Methylene Analog of N²- (<i>p</i>-n-Butylphenyl)-2′- deoxyguanosine 5′-Triphosphate: A Non-substrate Inhibitor of DNA Polymerases
  作者：Ivan Yanachkov、George E. Wright

  DOI：10.1080/15257779408013245

  日期：1994.3

  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.