2'-O-[4-(imidazolyl-1)butyl]-2-aminoadenosine | 160526-82-9

• 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'-O-[4-(imidazolyl-1)butyl]-2-aminoadenosine
• 英文别名: 2,6-diamino-9-[2'-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine；2,6-Diamino-9-[2-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purine；(2R,3R,4R,5R)-5-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)-4-(4-imidazol-1-ylbutoxy)oxolan-3-ol
• CAS: 160526-82-9
• 化学式: C₁₇H₂₄N₈O₄
• 分子量: 404.429
• InChiKey: AVOWFKRLPQBJLO-XNIJJKJLSA-N

物化性质

• 沸点：
  862.4±75.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O-[4-(imidazolyl-1)butyl]-2-aminoadenosine 在 sodium phosphate 、 adenosine deaminase 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 2'-O-[4-(imidazolyl-1)butyl]guanosine
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDES HAVING MODIFIED NUCLEOSIDE UNITS
  [FR] OLIGONUCLEOTIDES A UNITES NUCLEOSIDIQUES MODIFIEES

  摘要：

  揭示了包含一个或多个修饰核苷酸单元的寡核苷酸和寡核苷苷。这些寡核苷酸和寡核苷苷特别适用作为反义物质、核酶、适配体、siRNA物质、探针和引物，或者在与RNA杂交时，作为RNA裂解酶（包括RNase H和dsRNase）的底物。

  公开号：

  WO2003099840A1
• 作为产物：
  描述：

  1-(4-溴丁基)-咪唑 、 2-氨基腺嘌呤核苷 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 17.0h， 生成 2'-O-[4-(imidazolyl-1)butyl]-2-aminoadenosine
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDES HAVING MODIFIED NUCLEOSIDE UNITS
  [FR] OLIGONUCLEOTIDES A UNITES NUCLEOSIDIQUES MODIFIEES

  摘要：

  揭示了包含一个或多个修饰核苷酸单元的寡核苷酸和寡核苷苷。这些寡核苷酸和寡核苷苷特别适用作为反义物质、核酶、适配体、siRNA物质、探针和引物，或者在与RNA杂交时，作为RNA裂解酶（包括RNase H和dsRNase）的底物。

  公开号：

  WO2003099840A1

文献信息

• Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
  申请人：——

  公开号：US20020147160A1

  公开（公告）日：2002-10-10

  The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

  本发明提供了核苷化合物及其某些衍生物，这些衍生物是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，以及/或用于治疗丙型肝炎感染。本发明还描述了包含这种核苷化合物的药物组合物，单独使用或与其他对RNA依赖性RNA病毒感染，特别是HCV感染有效的制剂组合使用。还公开了使用本发明的核苷化合物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• Process for the preparation of 2'-O-alkyl purine phosphoramidites
  申请人：Isis Pharmceuticals, Inc.

  公开号：US05646265A1

  公开（公告）日：1997-07-08

  2'-O-alkylated guanosine, uridine, cytidine, and 2,6-diaminopurine 3'-O-phosphoramidites are prepared by alkylating nucleoside precursors, adding suitable blocking groups and phosphitylating. Alkylation is effected on 2,6-diamino-9-(.beta.-D-ribofuranosyl)purine followed by deamination to prepare guanosine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected on a dialkyl stannylene derivative of uridine to prepare uridine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on cytidine to prepare cytidine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on 2,6-diaminopurine to prepare 2,6-diaminopurine 2'-O-alkylated 3'-O-phosphormidites.

  2'-O-烷基化鸟苷、尿苷、胞苷和2,6-二氨基嘌呤3'-O-磷酰胺酯是通过烷基化核苷前体、添加适当的阻断基团和磷酰化来制备的。烷基化是在2,6-二氨基-9-(β-D-核糖呋喃基)嘌呤上进行的，随后进行去氨基化以制备鸟苷2'-O-烷基化3'-O-磷酰胺酯。烷基化是在尿苷的二烷基基锡衍生物上进行的，以制备尿苷2'-O-烷基化3'-O-磷酰胺酯。烷基化是直接在胞苷上进行的，以制备胞苷2'-O-烷基化3'-O-磷酰胺酯。烷基化是直接在2,6-二氨基嘌呤上进行的，以制备2,6-二氨基嘌呤2'-O-烷基化3'-O-磷酰胺酯。
• [EN] OLIGONUCLEOTIDES HAVING MODIFIED NUCLEOSIDE UNITS<br/>[FR] OLIGONUCLEOTIDES A UNITES NUCLEOSIDIQUES MODIFIEES
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2003099840A1

  公开（公告）日：2003-12-04

  Disclosed are oligonucleotides and oligonucleosides that include one or more modified nucleoside units. The oligonucleotides and oligonucleosides are particularly useful as antisense agents, ribozymes, aptamer, siRNA agents, probes and primers or, when hybridized to an RNA, as a substrate for RNA cleaving enzymes including RNase H and dsRNase.

  揭示了包含一个或多个修饰核苷酸单元的寡核苷酸和寡核苷苷。这些寡核苷酸和寡核苷苷特别适用作为反义物质、核酶、适配体、siRNA物质、探针和引物，或者在与RNA杂交时，作为RNA裂解酶（包括RNase H和dsRNase）的底物。
• Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase
  申请人：——

  公开号：US20040110717A1

  公开（公告）日：2004-06-10

  The present invention provides nucleoside derivatives which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside derivatives alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside derivatives of the present invention.

  本发明提供了一种核苷酸衍生物，其是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，和/或用于治疗丙型肝炎感染。该发明还描述了含有这种核苷酸衍生物的制药组合物，单独或与其他对RNA依赖性RNA病毒感染活性的制剂结合使用，特别是HCV感染。还揭示了使用本发明的核苷酸衍生物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• Process for the preparation of 2'-O-alkyl guanosine and related compounds
  申请人：ISIS Pharmaceuticals

  公开号：US05506351A1

  公开（公告）日：1996-04-09

  An improved process for preparing 2'-O-substituted guanosine comprising reacting an unprotected 2,6-diaminopurine riboside with an alkyl halide in the presence of a sodium hydride or a base of equal strength followed by a deamination step with adenosine deaminase. Such modified guanosine molecules can be used to synthesize 2'-O-modified oligonucleotides. The above alkylating process can also be used to prepare 3'-O-alkyl- and 2',3'-di-O-alkyl-2,6-diaminopurine ribosides. The deamination of these nucleosides yields the corresponding guanosine derivatives.

  一种改进的制备2'-O-取代鸟苷的方法，包括在氢氧化钠或等强碱的存在下，将未保护的2,6-二氨基嘌呤核苷与烷基卤素反应，随后进行腺苷脱氨酶的脱氨步骤。这种修改后的鸟苷分子可用于合成2'-O-修饰的寡核苷酸。上述烷基化过程也可用于制备3'-O-烷基-和2',3'-二-O-烷基-2,6-二氨基嘌呤核苷。这些核苷的脱氨作用会产生相应的鸟苷衍生物。