(2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydrofuran-3,4-diol | 690267-72-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydrofuran-3,4-diol
• 英文别名: (2R,3R,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol
• CAS: 690267-72-2
• 化学式: C₁₂H₁₄FN₉O₃
• 分子量: 351.3
• InChiKey: NICIHYMBBCGXIA-QMWPFBOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  L-苯丙氨醇 、 (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydrofuran-3,4-diol 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到GW328267X
  参考文献：
  名称：

  Efficient Synthesis of an Adenosine A2a Agonist:  Glycosylation of 2-Haloadenines and an N²-Alkyl-6-chloroguanine

  摘要：

  A convergent synthesis of adenosine A2a agonist 1 in the form of its maleate salt 2 was achieved. The key step in this approach was the highly selective 9beta-glycosylation reaction between 2-haloadenines or an N-2-alkyl-6-chloroguanine and a D-ribose derivative containing a 2-ethyltetrazolyl moiety. Glycosylations of other purine derivatives were also examined, and the methods developed provide efficient access to a variety of adenosine analogues such as 2-alkylaminoadenosines, an attractive class of compounds with antiinflammatory activity.

  DOI：

  10.1021/jo049963x
• 作为产物：
  描述：

  5-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(methyloxy)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-ethyl-2H-tetrazole 在 三氟甲磺酸三甲基硅酯 吡啶 、 甲醇 、 N,O-双三甲硅基乙酰胺 、 硫酸 、 potassium carbonate 、 乙酰氯 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 9.0h， 生成 (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Efficient Synthesis of an Adenosine A2a Agonist:  Glycosylation of 2-Haloadenines and an N²-Alkyl-6-chloroguanine

  摘要：

  A convergent synthesis of adenosine A2a agonist 1 in the form of its maleate salt 2 was achieved. The key step in this approach was the highly selective 9beta-glycosylation reaction between 2-haloadenines or an N-2-alkyl-6-chloroguanine and a D-ribose derivative containing a 2-ethyltetrazolyl moiety. Glycosylations of other purine derivatives were also examined, and the methods developed provide efficient access to a variety of adenosine analogues such as 2-alkylaminoadenosines, an attractive class of compounds with antiinflammatory activity.

  DOI：

  10.1021/jo049963x

文献信息

• 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
  申请人：——

  公开号：US20020086850A1

  公开（公告）日：2002-07-04

  There are provided according to the invention novel compounds of formula I 1 wherein R 1 , R 2 and R 3 are as described in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.

  根据本发明提供了一种新型化合物，其化学式为I1，其中R1、R2和R3如规范中所述，还提供了制备这些化合物的方法、含有它们的配方以及它们在治疗炎症性疾病中的用途。
• 2-(PURIN-9-YL)-TETRAHYDROFURAN-3,4-DIOL DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：EP0948509A1

  公开（公告）日：1999-10-13
• US6426337B1
  申请人：——

  公开号：US6426337B1

  公开（公告）日：2002-07-30
• US6528494B2
  申请人：——

  公开号：US6528494B2

  公开（公告）日：2003-03-04
• [EN] 2-(PURIN-9-YL)-TETRAHYDROFURAN-3,4-DIOL DERIVATIVES<br/>[FR] DERIVES DE 2-(PURINE-9-YL)-TETRAHYDROFURAN-3,4-DIOL
  申请人：GLAXO GROUP LIMITED

  公开号：WO1998028319A1

  公开（公告）日：1998-07-02

  (EN) There are provided according to the invention novel compounds of formula (I) wherein R1, R2 and R3 are as described in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.(FR) L'invention a trait à de nouveaux composés représentés par la formule (I), dans laquelle R1, R2 et R3 sont tels que décrits dans la description, à des procédés de préparation de ceux-ci, à des formulations les contenant et à leur utilisation dans des thérapies destinées au traitement de maladies inflammatoires.