(3R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydrofuran-3-ol | 1333503-75-5

• 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: (3R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydrofuran-3-ol
• 英文别名: (3R,5R)-5-(6-aminopurin-9-yl)tetrahydrofuran-3-ol；(3R,5R)-5-(6-aminopurin-9-yl)oxolan-3-ol
• CAS: 1333503-75-5
• 化学式: C₉H₁₁N₅O₂
• 分子量: 221.219
• InChiKey: CMOBHDZXOVIZAS-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 对甲苯基氯化亚硫代甲酸 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氨 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 135.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 (3R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036

文献信息

• Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides
  作者：Kiran S. Toti、Marco Derudas、Christopher McGuigan、Jan Balzarini、Serge Van Calenbergh

  DOI：10.1016/j.ejmech.2011.05.036

  日期：2011.9

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.