6-(Trifluoromethyl)purine | 2268-11-3

• 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: 6-(Trifluoromethyl)purine
• 英文别名: 6-(trifluoromethyl)-7H-purine
• CAS: 2268-11-3
• 化学式: C₆H₃F₃N₄
• mdl: MFCD11519443
• 分子量: 188.112
• InChiKey: RPGVDXOVVBWOIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(Trifluoromethyl)purine 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.0h， 生成 9-(2-deoxy-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
• 作为产物：
  描述：

  N-(6-oxo-4-trifluoromethyl-1,6-dihydro-pyrimidin-5-yl)-formamide 在 三氯氧磷 作用下， 生成 6-(Trifluoromethyl)purine
  参考文献：
  名称：

  Fluorine-containing Pyrimidines and Purines: Synthesis and Properties of Trifluoromethyl Pyrimidines and Purines¹

  摘要：

  DOI：

  10.1021/ja01554a041

文献信息

• Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside
  申请人：——

  公开号：US20020193314A1

  公开（公告）日：2002-12-19

  A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.

  通过磷酸解和异构化1-磷酸化糖衍生物的环式异构体混合物，有选择性地制备所需的异构体，同时通过结晶其中一种异构体以移动平衡。此外，利用核苷酸磷酸化酶的作用，从获得的1-磷酸化糖衍生物和一种改善立体选择性和更高产率的碱基中制备核苷酸。该过程是用于制备1-磷酸化糖衍生物和核苷酸的环式选择性过程。
• 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。
• [EN] 4'-C-ETHYNYL PURINE NUCLEOSIDES<br/>[FR] NUCLEOSIDES DE PURINE 4'-C-ETHYNYLE
  申请人：YAMASA CORP

  公开号：WO2000069877A1

  公开（公告）日：2000-11-23

  The invention provides 4'-C-ethynyl purine nucleosides represented by formula (I), wherein B represents a base selected from the group consisting of purine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  该发明提供了由式(I)表示的4'-C-乙炔基嘌呤核苷，其中B代表从嘌呤及其衍生物组成的群体中选择的碱基；X代表氢原子或羟基；而R代表氢原子或磷酸盐残基；以及含有任何一种化合物和药学上可接受的载体的制药组合物。最好，该组合物用作抗HIV剂或治疗艾滋病的药物。
• Selective process for producing an anomer of a 1-phosphorylated saccharide derivative and process for producing a nucleoside
  申请人：Komatsu Hironori

  公开号：US20060094869A1

  公开（公告）日：2006-05-04

  A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.

  通过磷酸解和异构化1-磷酸化糖衍生物的异构体混合物，有选择性地制备所需的异构体，并结晶其中一种异构体以移动平衡。此外，利用核苷酸磷酸化酶的作用，从所得的1-磷酸化糖衍生物和碱基中制备核苷，具有改善的立体选择性和更高的产量。该过程是一种选择性异构过程，用于制备1-磷酸化糖衍生物和核苷。
• 4'-C-ethynyl pyrimidine nucleoside compounds
  申请人：——

  公开号：US20020022722A1

  公开（公告）日：2002-02-21

  The invention provides 4′-C-ethynyl pyrimidine nucleosides (other than 4′-C-ethynylthymidine) represented by formula [I]: 1 wherein B represents a base selected from the group consisting of pyrimidine and derivatives thereof; X represents a hydrogen atom or a hydroxyl group; and R represents a hydrogen atom or a phosphate residue; and a pharmaceutical composition containing any one of the compounds and a pharmaceutically acceptable carrier. Preferably, the composition is used as an anti-HIV agent or a drug for treating AIDS.

  本发明提供了4'-C-乙炔基嘧啶核苷（不包括4'-C-乙炔基胸腺嘧啶）的化合物，其化学式为[I]：其中B代表从嘧啶和其衍生物中选择的碱基；X代表氢原子或羟基；R代表氢原子或磷酸残基；以及含有上述任一化合物和药学上可接受的载体的制药组合物。优选地，该组合物用作抗HIV剂或治疗艾滋病的药物。