Benzoic acid (2R,5S)-5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester | 201287-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: Benzoic acid (2R,5S)-5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester
• CAS: 201287-89-0
• 化学式: C₁₇H₁₅N₅O₃
• 分子量: 337.338
• InChiKey: HDVKCFLWGVHMKR-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,5S)-5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 以90%的产率得到beta-L-d4A
  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：

  [(2R,4S,5S)-4-acetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate 在 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 Benzoic acid (2R,5S)-5-(6-amino-purin-9-yl)-2,5-dihydro-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

文献信息

• 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.