N2-[Imidazol-1-yl-(propyl)]-2'-deoxyguanosine | 136834-40-7

• 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: N2-[Imidazol-1-yl-(propyl)]-2'-deoxyguanosine
• 英文别名: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(3-imidazol-1-ylpropylamino)-1H-purin-6-one
• CAS: 136834-40-7
• 化学式: C₁₆H₂₁N₇O₄
• 分子量: 375.387
• InChiKey: ULXUKKMJONSWOY-QJPTWQEYSA-N

物化性质

• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N2-[Imidazol-1-yl-(propyl)]-2'-deoxyguanosine 在 吡啶 、 ammonium hydroxide 、 TEA 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[2-(4-nitrophenyl)ethoxy]purin-2-yl]-N-(3-imidazol-1-ylpropyl)-2-methylpropanamide
  参考文献：
  名称：

  Remarkable enhancement of binding affinity of Heterocycle-modified DNA to DNA and RNA. Synthesis, characterization and biophysical evaluation of N2-imidazolylpropylguanine and N2-imidazolylpropyl-2-aminoadenine modified oligonucleotides

  摘要：

  Oligonucleotides containing novel N-2-Imidazolylpropylguanine and N-2-Imidazolylpropyl-2-aminoadenine moieties were synthesized and studied for their hybridization and biophysical properties. Interestingly, these heterocycle modified oligonucleotides showed a remarkable enhancement of heteroduplex binding affinity when hybridized to complementary DNA.

  DOI：

  10.1016/s0040-4039(00)76514-2
• 作为产物：
  描述：

  2,6-二氯-9-(3,5-二-O-对甲苯甲酰基-2-脱氧-beta-D-赤式-呋喃戊糖基)嘌呤 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 生成 N2-[Imidazol-1-yl-(propyl)]-2'-deoxyguanosine
  参考文献：
  名称：

  Remarkable enhancement of binding affinity of Heterocycle-modified DNA to DNA and RNA. Synthesis, characterization and biophysical evaluation of N2-imidazolylpropylguanine and N2-imidazolylpropyl-2-aminoadenine modified oligonucleotides

  摘要：

  Oligonucleotides containing novel N-2-Imidazolylpropylguanine and N-2-Imidazolylpropyl-2-aminoadenine moieties were synthesized and studied for their hybridization and biophysical properties. Interestingly, these heterocycle modified oligonucleotides showed a remarkable enhancement of heteroduplex binding affinity when hybridized to complementary DNA.

  DOI：

  10.1016/s0040-4039(00)76514-2

文献信息

• Oligonucleotides having chiral phosphorus linkages
  申请人：——

  公开号：US20010008936A1

  公开（公告）日：2001-07-19

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN 2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3′ position of a xylonucleotide. The reaction proceeds via inversion at the 3′ position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  本发明提供了具有高度纯的手性Sp磷酸硫酯、手性Rp磷酸硫酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯键的序列特异性寡核苷酸。新型寡核苷酸通过对木糖核苷酸的3'位置进行立体特异性的SN2亲核攻击制备而成，反应通过在木糖反应物种的3'位置进行反转，从而将磷酸二酯、磷酸硫酯、磷酸胺酯、磷酸三酯或烷基膦酸酯连接的核糖核苷糖基团并入寡核苷酸中。
• Compound for detecting and modulating RNA activity and gene expression
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06262241B1

  公开（公告）日：2001-07-17

  Compositions and methods for modulating the activity of RNA and DNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. Reactive portions which act, alternatively, through phosphorodiester bond cleavage, through backbone sugar bond cleavage or through base modification are preferrably employed. Groups which improve the pharmacodynamic and pharmacokinetic properties of the oligonucleotides are also useful in accordance with certain embodiments of this invention. Delivery of the reactive or non-reactive functionalities into the minor groove formed by the hybridization of the composition with the target RNA is also preferrably accomplished. Therapeutics, diagnostics and research methods and also disclosed. Synthetic nucleosides and nucleoside fragments are also provided useful for elaboration of oligonucleotides and oligonucleotide analogs for such purposes.

  本发明揭示了调节RNA和DNA活性的组合物和方法。根据优选实施例，制备了包含靶向部分和反应部分的反义组合物。反应部分可以通过磷酸二酯键断裂、骨架糖键断裂或碱基修饰等方式起作用。在本发明的某些实施例中，改善寡核苷酸的药效和药代动力学特性的基团也很有用。还可以通过将反应性或非反应性功能传递到与目标RNA杂交形成的小沟中来实现。本发明还揭示了治疗、诊断和研究方法。还提供了合成核苷酸和核苷酸片段，可用于制备寡核苷酸和寡核苷酸类似物。
• Compositions and methods for detecting and modulating rna activity and gene expression
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1418179A2

  公开（公告）日：2004-05-12

  Compositions and methods for modulating the activity of RNA and DNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. Reactive portions which act, alternatively, through phosphorodiester bond cleavage, through backbone sugar bond cleavage or through base modification are preferably employed. Groups which improve the pharmacodynamic and pharmacokinetic properties of the oligonucleotides are also useful in accordance with certain embodiments of this invention. Delivery of the reactive or non-reactive functionalities into the minor groove formed by the hybridization of the composition with the target RNA is also preferably accomplished. Therapeutics, diagnostics and research methods are also disclosed. Synthetic nucleosides and nucleoside fragments are also provided useful for elaboration of oligonucleotides and oligonucleotide analogs for such purposes.

  本文公开了调节 RNA 和 DNA 活性的组合物和方法。根据优选的实施方案，反义组合物由靶向部分和反应部分组成。反应部分最好通过磷酸二酯键裂解、骨架糖键裂解或碱基修饰起作用。根据本发明的某些实施方案，改善寡核苷酸药效学和药代动力学特性的基团也是有用的。最好还能将反应性或非反应性官能团输送到组合物与目标 RNA 杂交形成的次凹槽中。本发明还公开了治疗、诊断和研究方法。本发明还提供了合成核苷和核苷片段，可用于制备用于上述目的的寡核苷酸和寡核苷酸类似物。
• OLIGONUCLEOTIDE ANALOGS FOR DETECTING AND MODULATING RNA ACTIVITY AND GENE EXPRESSION
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0604409B1

  公开（公告）日：2004-07-14
• OLIGONUCLEOTIDES HAVING CHIRAL PHOSPHORUS LINKAGES
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0655088B1

  公开（公告）日：2002-07-24