9-(3-deoxy-β-D-ribofuranosyl)adenine | 170157-95-6

• 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: 9-(3-deoxy-β-D-ribofuranosyl)adenine
• 英文别名: cordycepin；3'-deoxy-adenosine；(2S,3S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 170157-95-6
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: OFEZSBMBBKLLBJ-KORWRZNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  9-(3-deoxy-β-D-ribofuranosyl)adenine 在 吡啶 、 甲醇 、 ammonium hydroxide 、 二苯基磷酸 、 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 [9-((2S,3S,5R)-3-Amino-5-trityloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-trityl-amine
  参考文献：
  名称：

  Unnatural β-L-Enantiomers of Nucleoside Analogues as Potent Anti-Hepatitis B Virus Agents

  摘要：

  Several 2'- or 3'-substituted 2',3'-dideoxy-beta-L-nucleosides bearing adenine as the base were stereospecifically synthesized and their antiviral properties examined. Two of them, namely 2'-azido- and 3'-azido-2',3'-dideoxy-beta-L-adenosine (2'-N-3-beta-L-ddA and 3'-N-3-beta-L-ddA) were found to have some anti-hepatitis B virus (HBV) activity in cell culture.

  DOI：

  10.1080/07328319808004708
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose 在 sodium methylate 、 四氯化锡 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 9-(3-deoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Unnatural β-L-Enantiomers of Nucleoside Analogues as Potent Anti-Hepatitis B Virus Agents

  摘要：

  Several 2'- or 3'-substituted 2',3'-dideoxy-beta-L-nucleosides bearing adenine as the base were stereospecifically synthesized and their antiviral properties examined. Two of them, namely 2'-azido- and 3'-azido-2',3'-dideoxy-beta-L-adenosine (2'-N-3-beta-L-ddA and 3'-N-3-beta-L-ddA) were found to have some anti-hepatitis B virus (HBV) activity in cell culture.

  DOI：

  10.1080/07328319808004708

文献信息

• Synthesis and Antiviral Evaluation of 3'-Deoxy-β-L-erythro-pentofuranosyl Nucleosides of the Five Naturally Occurring Nucleic Acid Bases
  作者：C. Mathé、G. Gosselin、M. -C. Bergogne、A. -M. Aubertin、G. Obert、A. Kirn、J. -L. Imbach

  DOI：10.1080/15257779508012424

  日期：1995.5.1

  of the protecting groups. All the prepared compounds were tested for their ability to inhibit the replication of a variety of DNA and RNA viruses (including HIV), but they did not show significant antiviral activity.

  摘要迄今未知的标题化合物是通过嘧啶和嘌呤苷元与适当的过酰基化的3'-脱氧-β-L-赤型戊呋喃糖进行糖基化立体立体合成的，然后除去保护基团。测试了所有制备的化合物抑制多种DNA和RNA病毒（包括HIV）复制的能力，但它们未显示出显着的抗病毒活性。