2'-deoxy-8-(1-heptyn-1-yl)adenosine | 156683-75-9

• 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'-deoxy-8-(1-heptyn-1-yl)adenosine
• 英文别名: (2R,3S,5R)-5-(6-amino-8-hept-1-ynyl-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；(2R,3S,5R)-5-(6-amino-8-hept-1-ynylpurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 156683-75-9
• 化学式: C₁₇H₂₃N₅O₃
• 分子量: 345.401
• InChiKey: MHPPOIPYUIABAQ-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-deoxy-8-(1-heptyn-1-yl)adenosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以85%的产率得到2'-deoxy-8-heptyladenosine
  参考文献：
  名称：

  Synthesis and Antiviral Activities of 8-Alkynyl-, 8-Alkenyl-, and 8-Alkyl-2'-deoxyadenosine Analogs

  摘要：

  Palladium-catalyzed cross-coupling of 8-bromo-2'-deoxyadenosine with terminal alkynes in the presence of copper(I) iodide in dimethylformamide resulted in a series of 8-(1-alkyn-1-yl)-2'-deoxyadenosines. Hydrogenation of alkynyl derivatives over 10 % Pd/C under atmospheric pressure gave 8-n-alkyl analogues in nearly quantitative yields. On partial saturation of heptynyl, pentynyl, and propynyl derivatives over Lindlar catalyst, the corresponding cis-olefins were obtained along with minor amounts of trans isomers. Of the analogues tested, the following showed some activity, i.e. they were found to be active at concentrations that were at least 3-fold lower than the cytotoxic concentrations: the 8-heptynyl derivative against vaccinia virus (VV), vesicular stomatitis virus (VSV), cytomegalovirus (CMV), and respiratory syncytial virus (RSV); the 8-propyl derivative against varicella-zoster virus (VZV) and CMV; the 8-pentyl derivative against CMV; the 8-heptyl derivative against VV, CMV, RSV, and influenza A; slid the 8-heptenyl derivative against VV, RSV, and influenza A. The unsubstituted 2'-deoxyadenosine did not show any antiviral effect, except against RSV. Except for 8-propyl-dA, the antivirally active dA analogues were rather inhibitory to the growth of human embryonic lung cells. The most cytotoxic was the 8-ethynyl derivative.

  DOI：

  10.1021/jm00035a010
• 作为产物：
  描述：

  1-庚炔 、 8-溴-2'-脱氧腺苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以81%的产率得到2'-deoxy-8-(1-heptyn-1-yl)adenosine
  参考文献：
  名称：

  Synthesis and Antiviral Activities of 8-Alkynyl-, 8-Alkenyl-, and 8-Alkyl-2'-deoxyadenosine Analogs

  摘要：

  Palladium-catalyzed cross-coupling of 8-bromo-2'-deoxyadenosine with terminal alkynes in the presence of copper(I) iodide in dimethylformamide resulted in a series of 8-(1-alkyn-1-yl)-2'-deoxyadenosines. Hydrogenation of alkynyl derivatives over 10 % Pd/C under atmospheric pressure gave 8-n-alkyl analogues in nearly quantitative yields. On partial saturation of heptynyl, pentynyl, and propynyl derivatives over Lindlar catalyst, the corresponding cis-olefins were obtained along with minor amounts of trans isomers. Of the analogues tested, the following showed some activity, i.e. they were found to be active at concentrations that were at least 3-fold lower than the cytotoxic concentrations: the 8-heptynyl derivative against vaccinia virus (VV), vesicular stomatitis virus (VSV), cytomegalovirus (CMV), and respiratory syncytial virus (RSV); the 8-propyl derivative against varicella-zoster virus (VZV) and CMV; the 8-pentyl derivative against CMV; the 8-heptyl derivative against VV, CMV, RSV, and influenza A; slid the 8-heptenyl derivative against VV, RSV, and influenza A. The unsubstituted 2'-deoxyadenosine did not show any antiviral effect, except against RSV. Except for 8-propyl-dA, the antivirally active dA analogues were rather inhibitory to the growth of human embryonic lung cells. The most cytotoxic was the 8-ethynyl derivative.

  DOI：

  10.1021/jm00035a010

文献信息

• COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF POXVIRUS INFECTIONS
  申请人：Chimerix, Inc.

  公开号：EP1868628A2

  公开（公告）日：2007-12-26
• Compounds, compositions and methods for the treatment of poxvirus infections
  申请人：Almond R. Merrick

  公开号：US20070003516A1

  公开（公告）日：2007-01-04

  The present application provides methods and compositions for combination therapy with antiviral compounds for the treatment of poxvirus infections, such as orthopox virus infections. In one embodiment, a method of treatment of a poxvirus infection is provided that comprises administering to a host in need thereof cidofovir, cyclic cidofovir, or a salt, ester, or prodrug thereof in combination or alternation with at least a second anti-poxvirus agent. The second anti-poxvirus agent is, for example, a biologic, such as a pegylated interferon.
• US8642577B2
  申请人：——

  公开号：US8642577B2

  公开（公告）日：2014-02-04
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF POXVIRUS INFECTIONS<br/>[FR] COMPOSES, COMPOSITIONS ET METHODES DE TRAITEMENT DES INFECTIONS A POXVIRUS
  申请人：CHIMERIX INC

  公开号：WO2006110655A2

  公开（公告）日：2006-10-19

  [EN] The present application provides methods and compositions for combination therapy with antiviral compounds for the treatment of poxvirus infections, such as orthopox virus infections. In one embodiment, a method of treatment of a poxvirus infection is provided that comprises administering to a host in need thereof cidofovir, cyclic cidofovir, or a salt, ester, or prodrug thereof in combination or alternation with at least a second anti-poxvirus agent. The second anti-poxvirus agent is, for example, a biologic, such as a pegylated interferon.
  [FR] L'invention concerne des méthodes et des compositions destinées au traitement combiné des infections à poxvirus telles que les infections à orthopoxvirus, par des composés antiviraux. Dans un mode de mise en oeuvre, la méthode de traitement d'une infection poxvirus consiste à administrer à un hôte nécessitant un tel traitement, du cidofovir, du cidofovir cyclique, ou un sel, un ester, ou un promédicament de celui-ci, en combinaison ou en alternance avec au moins un second agent anti-poxvirus. Le second agent anti-poxvirus peut être par exemple un agent biologique, tel qu'un interféron pégylé.