(2R,3R,4R,5R)-2-(2-amino-6-(methylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol | 714249-79-3

• 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-(2-amino-6-(methylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
• 英文别名: (3R,4R,5R)-2-(2-amino-6-(methylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol；(2R,3R,4R,5R)-2-[2-Amino-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol；(2R,3R,4R,5R)-2-[2-amino-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 714249-79-3
• 化学式: C₁₂H₁₈N₆O₄
• 分子量: 310.313
• InChiKey: WAHADTBHUZKERN-GSWPYSDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(2-amino-6-(methylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol 、 索非布韦中间体 在 叔丁基氯化镁 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以22%的产率得到(2S)-Isopropyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-(methylamino)-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino) propanoate
  参考文献：
  名称：

  [EN] 2'-SUBSTITUTED-N6-SUBSTITUTED PURINE NUCLEOTIDES FOR RNA VIRUS TREATMENT
  [FR] NUCLÉOTIDES DE PURINE SUBSTITUÉS EN POSITION 2'-N 6 POUR LE TRAITEMENT DU VIRUS À ARN

  摘要：

  描述的化合物或其药用盐或组合物的使用，用于治疗感染了除HCV之外的RNA病毒或其他在本文中更详细描述的疾病。

  公开号：

  WO2018048937A1
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (2R,3R,4R,5R)-2-(2-amino-6-(methylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Dual pro-drugs of 2′-C-methyl guanosine monophosphate as potent and selective inhibitors of hepatitis C virus

  摘要：

  We have previously reported the power of combining a 5'-phosphoramidate ProTide, phosphate prodrug, motif with a 6-methoxy purine pro-drug entity to generate highly potent anti-HCV agents, leading to agents in clinical trial. We herein extend this work with the disclosure that a variety of alternative 6-substituents are tolerated. Several compounds exceed the potency of the prior 6-methoxy leads, and in almost every case the ProTide is several orders of magnitude more potent than the parent nucleoside. We also demonstrate that these agents act as pro-drugs of 2'-C-methyl guanosine monophosphate. We have also reported the novel use of hepatocyte cell lysate as an ex vivo model for ProTide metabolism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.013

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。
• [EN] ORALLY-BIOAVAILABLE NUCLEOSIDE ANALOGS<br/>[FR] ANALOGUES DE NUCLÉOSIDES À BIODISPONIBILITÉ ORALE
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2022265964A1

  公开（公告）日：2022-12-22

  Described herein are orally-bioavailable nucleoside analogs and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of coronavirus infections, including SARS-CoV-2 infection.

  本文描述了口服生物可利用的核苷类似物和包含该化合物的制药组合物。这些化合物和组合物适用于治疗冠状病毒感染，包括SARS-CoV-2感染。
• 2'-SUBSTITUTED-N6-SUBSTITUTED PURINE NUCLEOTIDES FOR CORONA VIRUS TREATMENT
  申请人：ATEA Pharmaceuticals, Inc.

  公开号：EP3865136A1

  公开（公告）日：2021-08-18

  The use of described compounds or pharmaceutically acceptable salts or compositions thereof for the treatment of a host infected with an RNA virus other than HCV, or other disorder more fully described herein.

  将所述化合物或其药学上可接受的盐或组合物用于治疗感染了除 HCV 以外的 RNA 病毒的宿主或本文更全面描述的其他疾病。
• 2′-substituted-N6-substituted purine nucleotides for RNA virus treatment
  申请人：Atea Pharmaceuticals, Inc.

  公开号：US10946033B2

  公开（公告）日：2021-03-16

  The use of described compounds or pharmaceutically acceptable salts or compositions thereof for the treatment of a host infected with an RNA virus other than HCV, or other disorder more fully described herein.

  将所述化合物或其药学上可接受的盐或组合物用于治疗感染了除 HCV 以外的 RNA 病毒的宿主或本文更全面描述的其他疾病。