9-(β-D-ribofuranosyl)-6-(trifluoromethyl)purine | 76513-95-6

• 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-ribofuranosyl)-6-(trifluoromethyl)purine
• 英文别名: 6-(Trifluoromethyl)-9-(beta-D-ribofuranosyl)-9H-purine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(trifluoromethyl)purin-9-yl]oxolane-3,4-diol
• CAS: 76513-95-6
• 化学式: C₁₁H₁₁F₃N₄O₄
• 分子量: 320.228
• InChiKey: BNSOJNJWPPFFIF-KQYNXXCUSA-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

• 作为反应物：
  描述：

  9-(β-D-ribofuranosyl)-6-(trifluoromethyl)purine 在 吡啶 、 TEA 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(t-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-6-(trifluoromethyl)-purine
  参考文献：
  名称：

  Synthesis and Analysis of RNA Containing 6-Trifluoromethylpurine Ribonucleoside

  摘要：

  [GRAPHICS]We report the synthesis of a 5 ' -DMT-2 ' -TBDMS-protected phosphoramidite of 6-trifluoromethylpurine ribonucleoside (P-TFM) and its use in the site-specific incorporation of 6-trifluoromethyipurine into RNA. Properties of P-TFM-substituted RNA suggest it will be valuable in the study of RNA structure and the binding of RNA-modifying enzymes, particularly the RNA-editing adenosine deaminases.

  DOI：

  10.1021/ol016295i
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 9-(β-D-ribofuranosyl)-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

文献信息

• Studies on organic fluorine compounds. Part 35. Trifluoromethylation of pyrimidine- and purine-nucleosides with trifluoromethyl–copper complex
  作者：Yoshiro Kobayashi、Kenjiro Yamamoto、Toyohira Asai、Masanori Nakano、Itsumaro Kumadaki

  DOI：10.1039/p19800002755

  日期：——

  Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl–copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder. The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine

  使用三氟甲基-铜络合物的溶液将卤代的核苷衍生物进行三氟甲基化，该溶液是通过将三氟甲基碘和铜粉在六甲基磷酸三酰胺中振摇并滤出过量的铜粉而制得的。以中等至良好的产率获得以下三氟甲基化的核苷：5-三氟甲基-尿苷，-脱氧尿苷，-胞苷，-脱氧胞苷和-阿拉伯糖基胞嘧啶；8-三氟甲基-腺苷，-脱氧腺苷和-肌苷；和6-三氟甲基核呋喃呋喃糖基嘌呤。该程序提供了许多三氟甲基化合物的简单合成方法。
• 2-Substituted-6-trifluoromethyl purine derivatives with adenosine-A3 antagonistic activity
  申请人：Koch Melle

  公开号：US20060052331A1

  公开（公告）日：2006-03-09

  The present invention relates to 2-substituted-6-trifluoromethyl purine derivatives as selective adenosine antagonists, in particular adenosine-A 3 receptor antagonists, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said purine derivatives. The compounds have the general formula (1) wherein the symbols have the meanings given in the specification.

  本发明涉及作为选择性腺苷拮抗剂的2-取代-6-三氟甲基嘌呤衍生物，特别是腺苷A3受体拮抗剂，以及用于制备这些化合物的方法和用于合成所述嘌呤衍生物的新型中间体。这些化合物具有一般式（1），其中符号具有规范中给定的含义。
• Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues
  作者：Michal Hocek、Antonín Holý

  DOI：10.1135/cccc19990229

  日期：——

  A CuI/KF mediated perfluoroalkylation reaction of various 9-substituted 6-iodopurines 1 with trimethyl(trifluoromethyl)silane or heptafluoropropyl(trimethyl)silane was used for the synthesis of the corresponding 6-(trifluoromethyl)- and 6-(heptafluoropropyl)purine derivatives (purine bases, nucleosides and acyclic nucleotide analogues) in moderate to good yields.

  使用CuI/KF介导的全氟烷基化反应，将各种9-取代的6-碘嘌呤1与三甲基(三氟甲基)硅烷或七氟丙基(三甲基)硅烷反应，可合成相应的6-(三氟甲基)-和6-(七氟丙基)嘌呤衍生物(嘌呤碱基、核苷和非环核苷酸类似物)，收率中等至良好。
• 2-SUBSTITUTED-6-TRIFLUOROMETHYL PURINE DERIVATIVES WITH ADENOSINE-A3 ANTAGONISTIC ACTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1797092A1

  公开（公告）日：2007-06-20
• US7371737B2
  申请人：——

  公开号：US7371737B2

  公开（公告）日：2008-05-13