5'-mesyl-N²-(p-n-butylphenyl)-2'-deoxyguanosine | 160053-66-7

• 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: 5'-mesyl-N²-(p-n-butylphenyl)-2'-deoxyguanosine
• 英文别名: N²-(4-butylphenyl)-5'-mesyl-2'-deoxyguanosine；[(2R,3S,5R)-5-[2-(4-butylanilino)-6-oxo-3H-purin-9-yl]-3-hydroxyoxolan-2-yl]methyl methanesulfonate
• CAS: 160053-66-7
• 化学式: C₂₁H₂₇N₅O₆S
• 分子量: 477.541
• InChiKey: IPVRSQCVEUXYCL-GVDBMIGSSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  148.43
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-mesyl-N²-(p-n-butylphenyl)-2'-deoxyguanosine 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以98%的产率得到5'-azido-N²-(p-n-butylphenyl)-2',5'-dideoxyguanosine
  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
• 作为产物：
  描述：

  甲基磺酰氯 、 N-(4-丁基苯基)-2'-脱氧鸟苷 在 吡啶 作用下， 反应 0.5h， 以9.2%的产率得到3',5'-dimesyl-N²-(p-n-butylphenyl)-2'-deoxyguanosine
  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

• Nucleoside carbonyl(di- and triphosphates)Electronic supplementary information (ESI) available: figures showing the time course of the reaction of the phosphoroimidazolidate of BuPdGMP (2) with PCOP (6), and reaction of N-methylphosphoroimidazolate of BuPdGMP (4) with 1 eq. of 6. See http://www.rsc.org/suppdata/p1/b1/b102467c/
  作者：Ivan B. Yanachkov、James M. Stattel、George E. Wright

  DOI：10.1039/b102467c

  日期：2001.11.15

  The first examples of nucleoside di- and triphosphates containing the electrophilic and potentially reactive carbonyl group in place of a phosphoanhydride oxygen are reported, using the DNA polymerase inhibitors N2-(4-butylphenyl)-2′-deoxyguanosine 5′-triphosphate (BuPdGTP) and N2-(4-butylphenyl)-2′-deoxyguanosine 5′-diphosphate (BuPdGDP) as platforms. The P2,P3-carbonyltriphosphonate, BuPdGMPPCOP

  第一个例子 核苷 含有亲电性和潜在反应性的二磷酸酯和三磷酸酯 羰基 据报道，用磷代替氧酸酐 DNA聚合酶抑制剂 N 2-（4-丁基苯基）-2'-脱氧鸟苷5'-三磷酸酯 （BuPdGTP）和 N 2-（4-丁基苯基）-2'-脱氧鸟苷5'-二磷酸酯（BuPdGDP）作为平台。在P 2，P 3 -carbonyltriphosphonate，BuPdGMPPCOP，由phosphoro-之间反应得到Ñ单磷酸酯BuPdGMP的-methylimidazolidate和羰基二膦酸 （PCOP），并通过制备将其分离出来 反相色谱。羰基二膦酸酯类似物BuPdGMPCOP是通过用羰基二膦酸酯取代相应的5'-甲磺酰基核苷的5'-甲磺酰基而获得的。尽管BuPdGMPCOP在水溶液中稳定，但BuPdGMPPCOP水解为BuPdGMP和PCOP，半衰期为3小时。BuPdGMPPCOP和BuPdGMPCOP均具有强大的竞争力抑制剂