6-methylamino-9-[(5'-O-benzoyl-2',3'-O-isopropylidene)-4'-thio-β-D-ribofuranosyl]purine | 1203544-68-6

• 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-methylamino-9-[(5'-O-benzoyl-2',3'-O-isopropylidene)-4'-thio-β-D-ribofuranosyl]purine
• CAS: 1203544-68-6
• 化学式: C₂₁H₂₃N₅O₄S
• 分子量: 441.511
• InChiKey: AYFIGSKQASQGBU-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  100.39
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-methylamino-9-[(5'-O-benzoyl-2',3'-O-isopropylidene)-4'-thio-β-D-ribofuranosyl]purine 在 水 、 溶剂黄146 、 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 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：

  benzoic acid (3aS,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 、 盐酸甲胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以74%的产率得到6-methylamino-9-[(5'-O-benzoyl-2',3'-O-isopropylidene)-4'-thio-β-D-ribofuranosyl]purine
  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