2’,3’,5’-tri-O-acetyl-6-chloro-2-iodopurine riboside | 750644-58-7

• 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’,3’,5’-tri-O-acetyl-6-chloro-2-iodopurine riboside
• CAS: 750644-58-7
• 化学式: C₁₇H₁₆ClF₃N₄O₇
• 分子量: 480.785
• InChiKey: XBGQMROVONYODL-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  131.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2’,3’,5’-tri-O-acetyl-6-chloro-2-iodopurine riboside 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 (2R,3S,4S,5R)-2-(6-methylamino-2-trifluoromethyl-purin-9-yl)-5-hydroxymethyl-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Modulation of adenosine receptor affinity and intrinsic efficacy in adenine nucleosides substituted at the 2-position

  摘要：

  We studied the structural determinants of binding affinity and efficacy of adenosine receptor (AR) agonists. Substituents at the 2-position of adenosine were combined with N-6-substitutions known to enhance human A(3)AR affinity. Selectivity of binding of the analogues and their functional effects on cAMP production were studied using recombinant human A(1), A(2A), A(2B), and A(3)ARs. Mainly sterically small substituents at the 2-position modulated both the affinity and intrinsic efficacy at all subtypes. The 2-cyano group decreased hA(3)AR affinity and efficacy in the cases of N-6-(3-iodobenzyl) and N-6-(trans-2-phenyl-1-cyclopropyl), for which a full AAR agonist was converted into a selective antagonist; the 2-cyano-N-6-methyl analogue was a full A(3)AR agonist. The combination of N-6-benzyl and various 2-substitutions (chloro, trifluoromethyl, and cyano) resulted in reduced efficacy at the A(1)AR. The environment surrounding the 2-position within the putative A(3)AR binding site was explored using rhodopsin-based homology modeling and ligand docking. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.031
• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 在 吡啶 、 六甲基磷酰三胺 、 copper(l) iodide 、 亚硝酸特丁酯 、 二碘甲烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.5h， 生成 2’,3’,5’-tri-O-acetyl-6-chloro-2-iodopurine riboside
  参考文献：
  名称：

  Modulation of adenosine receptor affinity and intrinsic efficacy in adenine nucleosides substituted at the 2-position

  摘要：

  We studied the structural determinants of binding affinity and efficacy of adenosine receptor (AR) agonists. Substituents at the 2-position of adenosine were combined with N-6-substitutions known to enhance human A(3)AR affinity. Selectivity of binding of the analogues and their functional effects on cAMP production were studied using recombinant human A(1), A(2A), A(2B), and A(3)ARs. Mainly sterically small substituents at the 2-position modulated both the affinity and intrinsic efficacy at all subtypes. The 2-cyano group decreased hA(3)AR affinity and efficacy in the cases of N-6-(3-iodobenzyl) and N-6-(trans-2-phenyl-1-cyclopropyl), for which a full AAR agonist was converted into a selective antagonist; the 2-cyano-N-6-methyl analogue was a full A(3)AR agonist. The combination of N-6-benzyl and various 2-substitutions (chloro, trifluoromethyl, and cyano) resulted in reduced efficacy at the A(1)AR. The environment surrounding the 2-position within the putative A(3)AR binding site was explored using rhodopsin-based homology modeling and ligand docking. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.031

文献信息

• Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides
  作者：Kohsuke Aikawa、Yuzo Nakamura、Yuki Yokota、Wataru Toya、Koichi Mikami

  DOI：10.1002/chem.201405677

  日期：2015.1.2

  The aromatic perfluoroalkylation catalyzed by a copper(I) salt with bis(perfluoroalkyl)zinc reagents Zn(RF)2(DMPU)2, which were prepared and then isolated as a stable white powder from perfluoroalkyl iodide and diethylzinc, was accomplished to provide the perfluoroalkylated products in good‐to‐excellent yields. The advantages of this reliable and practical catalytic reaction are 1) air‐stable and easy‐to‐handle

  制备了铜（I）盐与双（全氟烷基）锌试剂Zn（R F）2（DMPU）2催化的芳族全氟烷基化反应，然后将其作为稳定的白色粉末从全氟烷基碘化物和二乙基锌中分离出来。全氟烷基化产品，收率优良。这种可靠，实用的催化反应的优点是：1）空气稳定且易于操作的双（全氟烷基）锌试剂可以使用； 2）该试剂具有反应性，因此无需活化剂和配体即可简单地进行操作； 3 ）不仅可以实现三氟甲基化，而且可以实现全氟烷基化。