9-(β-D-arabinofuranosyl)-6-(trifluoromethyl)purine

• 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: 9-(β-D-arabinofuranosyl)-6-(trifluoromethyl)purine
• 英文别名: (2R,3S,4S,5R)-2-(hydroxymethyl)-5-[6-(trifluoromethyl)purin-9-yl]oxolane-3,4-diol
• 化学式: C₁₁H₁₁F₃N₄O₄
• 分子量: 320.228
• InChiKey: BNSOJNJWPPFFIF-UHTZMRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-氯-2,3,5-三-O-苄基-D-阿拉伯呋喃糖 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 9-(β-D-arabinofuranosyl)-6-(trifluoromethyl)purine
  参考文献：
  名称：

  Synthesis and cytostatic activity of nucleosides and acyclic nucleoside analogues derived from 6-(trifluoromethyl)purines

  摘要：

  Glycosylation and alkylation of 6-(trifluoromethyl)purine by several protected halogenoses or hydroxyalkyl chlorides afforded regio- and stereoselectively the 9-beta-nucleosides or 9-alkylated purine derivatives in good yields. Deprotection of these intermediates gave a series of nucleoside (beta-D-ribofuranosyl, 2-deoxy-beta-D-ribofuranosyl and beta-D-arabinofuranosyl) and acyclonucleoside (2,3-dihydroxypropyl and (2-hydroxyethyl)oxymethyl) derivatives of 6-(trifluoromethyl)purine. While the ribofuranosyl derivative 1 showed significant cytostatic activity, the other derivatives were inactive. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00615-8