2,6-bis(3,5-dimethylpyrazol-1-yl)purineriboside | 1416446-74-6

• 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: 2,6-bis(3,5-dimethylpyrazol-1-yl)purineriboside
• 英文别名: (2R,3R,4S,5R)-2-[2,6-bis(3,5-dimethylpyrazol-1-yl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1416446-74-6
• 化学式: C₂₀H₂₄N₈O₄
• 分子量: 440.462
• InChiKey: FGLVXFAFZHNQSY-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,6-bis(3,5-dimethylpyrazol-1-yl)purineriboside 在 氨 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 40.0h， 生成 2-(3,5-dimethylpyrazol-1-yl)inosine
  参考文献：
  名称：

  Metal-Ion-Mediated Base Pairing between Natural Nucleobases and Bidentate 3,5-Dimethylpyrazolyl-Substituted Purine Ligands

  摘要：

  The potential of three modified purine bases, namely, 6-(3,5-dimethylpyrazol-1-yl)purine, 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine, and 2-(3,5-dimethylpyrazol-1-yl)adenine, for metal-ion-mediated base pairing within an oligonucleotide environment has been investigated. The respective modified nucleosides were incorporated in the middle of 9-mer 2'-O-methyl oligonucleotides and the hybridization of these modified oligonucleotides with their unmodified counterparts studied by UV and CD spectrometry in the absence and presence of Cu2+ or Zn2+. All of the modified oligonucleotides formed more stable duplexes in the presence of divalent metal ions than in the absence thereof, but with different preferences for the complementary oligonucleotide. The oligonucleotide incorporating 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine readily accepted any of the natural nucleobases opposite to this modified base regardless of whether Cu2+ or Zn2+ was used as the bridging metal ion. The other two oligonucleotides, on the other hand, were much more discriminating, exhibiting markedly elevated Tm values only in the presence of Cu2+ and only when certain natural nucleobases were paired with the modified one. The origin of the selectivity (or promiscuity) of the metal-ion-mediated base pairing is discussed in terms of the ability of the modified nucleobases, as well as their natural counterparts, to serve as anionic ligands.

  DOI：

  10.1021/jo501237r

文献信息

• Formation of Mixed-Ligand Complexes of Pd2+ with Nucleoside 5'-Monophosphates and Some Metal-Ion-Binding Nucleoside Surrogates
  作者：Oleg Golubev、Tuomas Lönnberg、Harri Lönnberg

  DOI：10.3390/molecules191016976

  日期：——

  Formation of mixed-ligand Pd2+ complexes between canonical nucleoside 5'-monophosphates and five metal-ion-binding nucleoside analogs has been studied by 1H-NMR spectroscopy to test the ability of these nucleoside surrogates to discriminate between unmodified nucleobases by Pd2+-mediated base pairing. The nucleoside analogs studied included 2,6-bis(3,5-dimethylpyrazol-1-yl)-, 2,6-bis(1-methylhydrazinyl)- and 6-(3,5-dimethylpyrazol-1-yl)-substituted 9-(β-d-ribofuranosyl)purines 1–3, and 2,4-bis(3,5-dimethylpyrazol-1-yl)- and 2,4-bis(1-methylhydrazinyl)-substituted 5-(β-d-ribofuranosyl)-pyrimidines 4–5. Among these, the purine derivatives 1-3 bound Pd2+ much more tightly than the pyrimidine derivatives 4, 5 despite apparently similar structures of the potential coordination sites. Compounds 1 and 2 formed markedly stable mixed-ligand Pd2+ complexes with UMP and GMP, UMP binding favored by 1 and GMP by 2. With 3, formation of mixed-ligand complexes was retarded by binding of two molecules of 3 to Pd2+.

  通过1H-NMR光谱研究了在标准核苷5'-单磷酸和五种金属离子结合核苷类似物之间形成混合配体Pd2+复合物，以测试这些核苷替代物通过Pd2+介导的碱基配对区分未修饰核苷碱基的能力。研究的核苷类似物包括2,6-双(3,5-二甲基吡唑-1-基)-、2,6-双(1-甲基肼基)-和6-(3,5-二甲基吡唑-1-基)-取代的9-(β-d-呋喃核糖基)嘌呤1-3，以及2,4-双(3,5-二甲基吡唑-1-基)-和2,4-双(1-甲基肼基)-取代的5-(β-d-呋喃核糖基)嘧啶4-5。其中，嘌呤衍生物1-3与Pd2+的结合比嘧啶衍生物4、5更紧密，尽管潜在配位位点的结构明显相似。化合物1和2与UMP和GMP形成了明显稳定的混合配体Pd2+复合物，UMP与1结合，GMP与2结合。对于3，由于两个3