2-fluoro-9-(2-azido-2-deoxy-β-D-arabinofuranosyl)purin-6-amine | 111557-03-0

• 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: 2-fluoro-9-(2-azido-2-deoxy-β-D-arabinofuranosyl)purin-6-amine
• 英文别名: (2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-4-azido-2-(hydroxymethyl)oxolan-3-ol
• CAS: 111557-03-0
• 化学式: C₁₀H₁₁FN₈O₃
• 分子量: 310.248
• InChiKey: SDUZYYWZYYMSFB-AYQXTPAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-fluoro-9-(2-azido-2-deoxy-β-D-arabinofuranosyl)purin-6-amine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以45%的产率得到2-fluoro-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purin-6-amine
  参考文献：
  名称：

  Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine

  摘要：

  The synthesis of a series of 2-chloro- or 2-fluoro-9-(2-substituted-2-deoxy-beta-D-arabinofuranosyl)adenines (4g-n) is described. New compounds were prepared from either 2-chloroadenosine or 2-fluoroadenosine by first blocking the 3'- and 5'-hydroxyls as the tetraisopropyldisiloxane derivatives. Activation of O-2' by formation of a triflate followed by nucleophilic displacement allowed introduction of various groups in the proper configuration at C-2'. Fluoride ion treatment then produced the deblocked nucleosides. All of the new compounds were evaluated as cytotoxic agents against L1210 and H.Ep.-2 cells and as antiviral agents against herpes simplex viruses 1 and 2 and vaccinia virus in culture.

  DOI：

  10.1021/jm00397a024
• 作为产物：
  描述：

  2-fluoro-2'-O-<(trifluoromethyl)sulfonyl>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 在 叠氮化锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-fluoro-9-(2-azido-2-deoxy-β-D-arabinofuranosyl)purin-6-amine
  参考文献：
  名称：

  Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine

  摘要：

  The synthesis of a series of 2-chloro- or 2-fluoro-9-(2-substituted-2-deoxy-beta-D-arabinofuranosyl)adenines (4g-n) is described. New compounds were prepared from either 2-chloroadenosine or 2-fluoroadenosine by first blocking the 3'- and 5'-hydroxyls as the tetraisopropyldisiloxane derivatives. Activation of O-2' by formation of a triflate followed by nucleophilic displacement allowed introduction of various groups in the proper configuration at C-2'. Fluoride ion treatment then produced the deblocked nucleosides. All of the new compounds were evaluated as cytotoxic agents against L1210 and H.Ep.-2 cells and as antiviral agents against herpes simplex viruses 1 and 2 and vaccinia virus in culture.

  DOI：

  10.1021/jm00397a024

文献信息

• SECRIST, JOHN A.;SHORTNACY, ANITA T.;MONTGOMERY, JOHN A., J. MED. CHEM., 31,(1988) N 2, 405-410
  作者：SECRIST, JOHN A.、SHORTNACY, ANITA T.、MONTGOMERY, JOHN A.

  DOI：——

  日期：——