2-chloro-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purin-6-amine | 111557-02-9

• 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-chloro-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purin-6-amine
• 英文别名: (2R,3S,4S,5R)-4-amino-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 111557-02-9
• 化学式: C₁₀H₁₃ClN₆O₃
• 分子量: 300.705
• InChiKey: HZSUPBZMAVCLJF-AYQXTPAHSA-N

物化性质

• 沸点：
  628.1±65.0 °C(Predicted)
• 密度：
  2.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 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：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-chloro-9-<2-azido-2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>purin-6-amine 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 2-chloro-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

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：——