[(2R,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate | 201287-86-7

• 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,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate
• CAS: 201287-86-7
• 化学式: C₁₉H₁₉N₅O₅
• 分子量: 397.39
• InChiKey: GUNGCOPBVXKKHA-GLJUWKHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  131.45
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(2R,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate 在 sodium methylate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 Benzoic acid (2R,4S,5S)-5-(6-amino-purin-9-yl)-4-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Anti-human immunodeficiency and anti-hepatitis B virus activities of β-l-2′,3′-dideoxy purine nucleosides

  摘要：

  beta-L-2',3'-Dideoxyadenosine, beta-L-2',3'-didehydro-2',3'-dideoxyadenosine and related compounds were synthesized in a stereoselective manner. These compounds were tested in vitro against HBV in 2.2.15 cell line and against HIV-1 in PBM and CEM cells. It was found that beta-L-2',3'-didehydro-2',3'-dideoxyadenosine (7) exhibited significant anti-HIV (EC(50) 0.38 mu M in PBM cells) and anti-HBV activity (EC(50) 1.2 mu M). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00293-4
• 作为产物：
  描述：

  腺嘌呤 、 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 以62%的产率得到[(2R,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Anti-human immunodeficiency and anti-hepatitis B virus activities of β-l-2′,3′-dideoxy purine nucleosides

  摘要：

  beta-L-2',3'-Dideoxyadenosine, beta-L-2',3'-didehydro-2',3'-dideoxyadenosine and related compounds were synthesized in a stereoselective manner. These compounds were tested in vitro against HBV in 2.2.15 cell line and against HIV-1 in PBM and CEM cells. It was found that beta-L-2',3'-didehydro-2',3'-dideoxyadenosine (7) exhibited significant anti-HIV (EC(50) 0.38 mu M in PBM cells) and anti-HBV activity (EC(50) 1.2 mu M). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00293-4

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。
• New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities
  作者：G. Gosselin、V. Boudou、J.-F. Griffon、G. Pavia、C. Pierra、J.-L. Imbach、A.-M. Aubertin、R. F. Schinazi、A. Faraj、J.-P. Sommadossi

  DOI：10.1080/07328319708006190

  日期：1997.7

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.
• Unnatural β-L-Enantiomers of Nucleoside Analogues as Potent Anti-Hepatitis B Virus Agents
  作者：G. Gosselin、V. Boudou、J-F Griffon、G. Pavia、C. Pierra、J-L Imbach、A. Faraj、J-P Sommadossi

  DOI：10.1080/07328319808004708

  日期：1998.9

  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.