6-cyclopropylamino-9-(2,3-dideoxy-β-D-glyceropentofuranosyl)-9H-purine | 120503-31-3

• 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: 6-cyclopropylamino-9-(2,3-dideoxy-β-D-glyceropentofuranosyl)-9H-purine
• 英文别名: Adenosine, N-cyclopropyl-2',3'-dideoxy-；[(2S,5R)-5-[6-(cyclopropylamino)purin-9-yl]oxolan-2-yl]methanol
• CAS: 120503-31-3
• 化学式: C₁₃H₁₇N₅O₂
• 分子量: 275.31
• InChiKey: IZKSHNCTSLXXDD-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 palladium on activated charcoal 硫酸氢铵 、 sodium hydroxide 、 TMSTf 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 85.0h， 生成 6-cyclopropylamino-9-(2,3-dideoxy-β-D-glyceropentofuranosyl)-9H-purine
  参考文献：
  名称：

  Adenine and Deazaadenine Nucleoside and Deoxynucleoside Analogues: Inhibition of Viral Replication of Sheep MVV (In Vitro Model for HIV) and Bovine BHV-1

  摘要：

  A series of N-6-cycloalkyl-2',3'-dideoxyadenosine derivatives has been prepared by coupling of 2,6-dichloropurine to protected 2,3-dideoxyribose. followed by reaction with appropriate cycloalkylamines. Synthesized compounds, along with other purine nucleoside analogues previously synthesized in our laboratory. have been tested for their antiviral activity against Bovine herpesvirus 1 (BHV-1) and sheep Maedi/Visna Virus (MVV). the latter being an in vitro and in vivo model of Human Immunodeficiency Virus (HIV). All compounds showed good antireplicative activity against MVV. with the N-6-cycloheptyl-2'.3-dideoxy-adenosine (5b) being the most active [effective concentration (EC50) causing 50% reduction of cytopatic effects (CP) = 27 nM]. All compounds showed also a from tow to very low cell toxicity. resulting in a cytotoxic dose 50 (CD50)/EC50 ratio in some cases higher than 1000. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00131-1

文献信息

• Deaza- and Deoxyadenosine Derivatives: Synthesis and Inhibition of Animal Viruses as Human Infection Models
  作者：Sauro Vittori、Daniela Salvatori、Rosaria Volpini、Silvia Vincenzetti、Alberto Vita、Sara Taffi、Stefano Costanzi、Catia Lambertucci、Gloria Cristalli

  DOI：10.1081/ncn-120022676

  日期：2003.10

  N-6-Cycloalkyl-2',3'-dideoxyadenosine derivatives and (2-chloro)-N-6-cycloheptyl-3-deazaadenosine have been synthesized and tested, along with other (deaza)purine (deoxy)nucleosides from our chemical library, as inhibitors of virus replication against Bovine Herpes Virus 1 (BHV-1) and sheep Maedi/Visna Virus (MVV). Most compounds demonstrated good antireplicative activity against MVV, showing also low cell toxicity.
• Adenine and Deazaadenine Nucleoside and Deoxynucleoside Analogues: Inhibition of Viral Replication of Sheep MVV (In Vitro Model for HIV) and Bovine BHV-1
  作者：Daniela Salvatori、Rosaria Volpini、Silvia Vincenzetti、Alberto Vita、Stefano Costanzi、Catia Lambertucci、Gloria Cristalli、Sauro Vittori

  DOI：10.1016/s0968-0896(02)00131-1

  日期：2002.9

  A series of N-6-cycloalkyl-2',3'-dideoxyadenosine derivatives has been prepared by coupling of 2,6-dichloropurine to protected 2,3-dideoxyribose. followed by reaction with appropriate cycloalkylamines. Synthesized compounds, along with other purine nucleoside analogues previously synthesized in our laboratory. have been tested for their antiviral activity against Bovine herpesvirus 1 (BHV-1) and sheep Maedi/Visna Virus (MVV). the latter being an in vitro and in vivo model of Human Immunodeficiency Virus (HIV). All compounds showed good antireplicative activity against MVV. with the N-6-cycloheptyl-2'.3-dideoxy-adenosine (5b) being the most active [effective concentration (EC50) causing 50% reduction of cytopatic effects (CP) = 27 nM]. All compounds showed also a from tow to very low cell toxicity. resulting in a cytotoxic dose 50 (CD50)/EC50 ratio in some cases higher than 1000. (C) 2002 Elsevier Science Ltd. All rights reserved.