(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate | 333333-74-7

• 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: (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate
• 英文别名: (2R,3S,4S,5R)-2-(6-chloro-2-cyano-purin-9-yl)-3,4-diacetoxy-5-acetoxymethyl-tetrahydrofuran；(2R,3R,4R,5R)-4-acetyloxy-2-acetyloxymethyl-5-(6-chloro-2-cyano-9H-purin-9-yl)-tetrahydro-3-furanyl acetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloro-2-cyanopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 333333-74-7
• 化学式: C₁₇H₁₆ClN₅O₇
• 分子量: 437.796
• InChiKey: YZOVTVHHQBYENK-IWCJZZDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate 在 三乙胺 作用下， 生成 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate
  参考文献：
  名称：

  Purine derivatives

  摘要：

  本发明涉及具有公式1的化合物，以及药用可接受的盐和溶剂化物，还涉及用于制备这些化合物的过程、在制备中使用的中间体，以及包含这些化合物的组合物，以及这些化合物作为腺苷A2a受体激动剂的使用。

  公开号：

  US20020032168A1
• 作为产物：
  描述：

  2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 亚硝酸特丁酯 、 三(2-呋喃基)膦 、 二碘甲烷 、 1,1,3,3-四甲基脲 作用下， 以 乙腈 为溶剂， 反应 25.0h， 生成 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate
  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

• [EN] PURINE DERIVATIVES<br/>[FR] DERIVES DE PURINE
  申请人：PFIZER LTD

  公开号：WO2002000676A1

  公开（公告）日：2002-01-03

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, to processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds as adenosine A2a receptor agonists.

  本发明涉及式（I）化合物及其药学上可接受的盐和溶剂化物，制备过程中使用的中间体，以及含有此类化合物的组合物和将此类化合物用作腺苷A2a受体激动剂的用途。
• PURINE DERIVATIVES
  申请人：Pfizer Limited

  公开号：EP1220863B1

  公开（公告）日：2003-04-23
• US6350735B1
  申请人：——

  公开号：US6350735B1

  公开（公告）日：2002-02-26
• US6921753B2
  申请人：——

  公开号：US6921753B2

  公开（公告）日：2005-07-26
• US7238676B2
  申请人：——

  公开号：US7238676B2

  公开（公告）日：2007-07-03