(2S,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrothiophene-2-carboxylic acid | 1203544-74-4

• 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: (2S,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrothiophene-2-carboxylic acid
• CAS: 1203544-74-4
• 化学式: C₂₃H₄₁N₅O₄SSi₂
• 分子量: 539.847
• InChiKey: QVRDNSCUUHZYGU-PFRQMTDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  111.39
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrothiophene-2-carboxylic acid 、 盐酸甲胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Design and synthesis of N6-substituted-4′-thioadenosine-5′-uronamides as potent and selective human A3 adenosine receptor agonists

  摘要：

  On the basis of a bioisosteric rationale, 4'-thionucleoside analogues of IB-MECA (N-6-(3-Iodo-benzyl)-9-(5'-methylaminocarbonyl-beta-D-ribofuranosyl)adenine), which is a potent and selective A(3) adenosine receptor (AR) agonist, were synthesized from D-gulonic acid gamma-lactone. The 4'-thio analogue (5h) of IB-MECA showed extremely high binding affinity (K-i = 0.25 nM) at the human A(3)AR and was more potent than IB-MECA (K-i = 1.4 nM). Bulky substituents at the 5'-uronamide position, such as cyclohexyl and 2-methylbenzyl, in this series of 2-H nucleoside derivatives were tolerated in A3AR binding, although small alkyl analogues were more potent. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.011
• 作为产物：
  描述：

  在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrothiophene-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of N6-substituted-4′-thioadenosine-5′-uronamides as potent and selective human A3 adenosine receptor agonists

  摘要：

  On the basis of a bioisosteric rationale, 4'-thionucleoside analogues of IB-MECA (N-6-(3-Iodo-benzyl)-9-(5'-methylaminocarbonyl-beta-D-ribofuranosyl)adenine), which is a potent and selective A(3) adenosine receptor (AR) agonist, were synthesized from D-gulonic acid gamma-lactone. The 4'-thio analogue (5h) of IB-MECA showed extremely high binding affinity (K-i = 0.25 nM) at the human A(3)AR and was more potent than IB-MECA (K-i = 1.4 nM). Bulky substituents at the 5'-uronamide position, such as cyclohexyl and 2-methylbenzyl, in this series of 2-H nucleoside derivatives were tolerated in A3AR binding, although small alkyl analogues were more potent. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.011