(2R,3R,4R,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol | 582313-58-4

• 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: (2R,3R,4R,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
• 英文别名: Adenosine, 2-fluoro-2a(2)-C-methyl-；(2R,3R,4R,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 582313-58-4
• 化学式: C₁₁H₁₄FN₅O₄
• 分子量: 299.262
• InChiKey: PLKRCVTXQHGOJJ-GITKWUPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 在 磷酸三甲酯 、 三氯氧磷 、 三正丁胺 、 四丁基高氯酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 ((2R,3R,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
  参考文献：
  名称：

  Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

  摘要：

  A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

  DOI：

  10.1021/acsmedchemlett.5b00402
• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以269 mg的产率得到(2R,3R,4R,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

  摘要：

  A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

  DOI：

  10.1021/acsmedchemlett.5b00402

文献信息

• [EN] METHODS OF INHIBITING ORTHOPOXVIRUS REPLICATION WITH NUCLEOSIDE COMPOUNDS<br/>[FR] PROCEDE D'INHIBITION DE LA REPLICATION D'ORTHOPOXVIRUS AVEC DES COMPOSES DE NUCLEOSIDE
  申请人：MERCK & CO INC

  公开号：WO2003068244A1

  公开（公告）日：2003-08-21

  The present invention provides methods of inhibiting orthopoxvirus replication and/or treating orthopoxvirus infection with certain nucleoside compounds and derivatives thereof. These compounds are particularly useful as inhibitors of vaccinia virus and variola virus replication and/or for the treatment of vaccinia virus and variola virus infection. The nucleoside compounds may be administered alone or in combination with other agents active against orthopoxvirus infection, in particular against vaccinia virus or variola virus infection. Another aspect of the present invention provides for the use of such nucleoside compounds in the manufacture of a medicament for the inhibition of orthopoxvirus replication and/or for the treatment of orthopoxvirus infection. Yet a further aspect of the present invention provides such nucleoside compounds for use as a medicament for the inhibition of orthopoxvirus replication and/or for the treatment of orthopoxvirus infection.

  本发明提供了使用某些核苷类化合物及其衍生物抑制正痘病毒复制和/或治疗正痘病毒感染的方法。这些化合物特别适用于抑制天花病毒和痘病毒的复制和/或治疗天花病毒和痘病毒感染。这些核苷类化合物可以单独或与其他对抗正痘病毒感染的药物联合使用，特别是对抗天花病毒或痘病毒感染的药物。本发明的另一个方面提供了将这些核苷类化合物用于制造药物，以抑制正痘病毒复制和/或治疗正痘病毒感染。本发明的另一个方面提供了这些核苷类化合物作为药物，以抑制正痘病毒复制和/或治疗正痘病毒感染。
• Methods of inhibiting orthopoxvirus replication with nucleoside compounds
  申请人：Olsen B. David

  公开号：US20050164960A1

  公开（公告）日：2005-07-28

  The present invention provides methods of inhibiting orthopoxvirus replication and/or treating orthopoxvirus infection with certain nucleoside compounds and derivatives thereof. These compounds are particularly useful as inhibitors of vaccinia virus and variola virus replication and/or for the treatment of vaccinia virus and variola virus infection. The nucleoside compounds may be administered alone or in combination with other agents active against orthopoxvirus infection, in particular against vaccinia virus or variola virus infection. Another aspect of the present invention provides for the use of such nucleoside compounds in the manufacture of a medicament for the inhibition of orthopoxvirus replication and/or for the treatment of orthopoxvirus infection. Yet a further aspect of the present invention provides such nucleoside compounds for use as a medicament for the inhibition of orthopoxvirus replication and/or for the treatment of orthopoxvirus infection.

  本发明提供了使用某些核苷类化合物及其衍生物来抑制正痘病毒复制和/或治疗正痘病毒感染的方法。这些化合物特别适用于抑制天花病毒和痘病毒的复制和/或治疗天花病毒和痘病毒感染。这些核苷类化合物可以单独或与其他对抗正痘病毒感染的药物联合使用，特别是对抗天花病毒或痘病毒感染的药物。本发明的另一方面提供了将这些核苷类化合物用于制造用于抑制正痘病毒复制和/或治疗正痘病毒感染的药物。本发明的另一个方面提供了这些核苷类化合物作为用于抑制正痘病毒复制和/或治疗正痘病毒感染的药物。
• EP1476169A4
  申请人：——

  公开号：EP1476169A4

  公开（公告）日：2009-06-03
• METHODS OF INHIBITING ORTHOPOXVIRUS REPLICATION WITH NUCLEOSIDE COMPOUNDS
  申请人：Merck & Co., Inc.

  公开号：EP1476169A1

  公开（公告）日：2004-11-17
• SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF
  申请人：Janssen BioPharma, Inc.

  公开号：US20190169221A1

  公开（公告）日：2019-06-06

  Disclosed herein are nucleotide analogs, methods of synthesizing nucleotide analogs and methods of treating diseases and/or conditions such as a Picornaviridae and/or Flaviviridae viral infections with one or more nucleotide analogs.