8-cyclopentyl-3-(3-(4-fluorosulfonylbenzamido)propyl)-1-propyl-7-(2-(trimethylsilyl)ethoxymethyl)xanthine | 321907-02-2

• 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: 8-cyclopentyl-3-(3-(4-fluorosulfonylbenzamido)propyl)-1-propyl-7-(2-(trimethylsilyl)ethoxymethyl)xanthine
• 英文别名: 4-[3-[8-Cyclopentyl-2,6-dioxo-1-propyl-7-(2-trimethylsilylethoxymethyl)purin-3-yl]propylcarbamoyl]benzenesulfonyl fluoride
• CAS: 321907-02-2
• 化学式: C₂₉H₄₂FN₅O₆SSi
• 分子量: 635.832
• InChiKey: CWQOKQJGOVHRIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-cyclopentyl-3-(3-(4-fluorosulfonylbenzamido)propyl)-1-propyl-7-(2-(trimethylsilyl)ethoxymethyl)xanthine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以71%的产率得到4-[3-(8-Cyclopentyl-2,6-dioxo-1-propyl-1,2,6,7-tetrahydro-purin-3-yl)-propylcarbamoyl]-benzenesulfonyl fluoride
  参考文献：
  名称：

  Fluorosulfonyl-Substituted Xanthines as Selective Irreversible Antagonists for the A₁-Adenosine Receptor

  摘要：

  FSCPX (1) has been reported to be a potent, selective, and irreversible antagonist for the A(1)-adenosine receptor (AR). To obtain an irreversible A(1)AR antagonist with potentially better stability and to further elucidate the effects of linker structure on the pharmacological characteristics, several new analogues were targeted in which the labile ester linkage of 1 was replaced by more stable functionalities. In particular, alkyl and:amide linkers between the xanthine pharmacophore and the reactive 4-fluorosulfonylphenyl group were explored. The data showed that the chemical composition of the linker affects the affinity and apparent irreversible binding to the A(1)AR. Overall, compound 23b appeared to have the most advantageous characteristics as a potential irreversible ligand for the A(1)AR. These include relatively high affinity for the A(1)AR. as compared to the A(2A)AR, concentration-dependent and selective apparent irreversible binding to the A(1)AR, and ease;of removal of unbound ligand from biological membranes. These :properties indicate that 23b has the potential to be a useful tool for further study of the structure and function of the A(1)AR.

  DOI：

  10.1021/jm000181f
• 作为产物：
  描述：

  4-(氟磺酰)苯甲酸 在 potassium carbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 8-cyclopentyl-3-(3-(4-fluorosulfonylbenzamido)propyl)-1-propyl-7-(2-(trimethylsilyl)ethoxymethyl)xanthine
  参考文献：
  名称：

  Fluorosulfonyl-Substituted Xanthines as Selective Irreversible Antagonists for the A₁-Adenosine Receptor

  摘要：

  FSCPX (1) has been reported to be a potent, selective, and irreversible antagonist for the A(1)-adenosine receptor (AR). To obtain an irreversible A(1)AR antagonist with potentially better stability and to further elucidate the effects of linker structure on the pharmacological characteristics, several new analogues were targeted in which the labile ester linkage of 1 was replaced by more stable functionalities. In particular, alkyl and:amide linkers between the xanthine pharmacophore and the reactive 4-fluorosulfonylphenyl group were explored. The data showed that the chemical composition of the linker affects the affinity and apparent irreversible binding to the A(1)AR. Overall, compound 23b appeared to have the most advantageous characteristics as a potential irreversible ligand for the A(1)AR. These include relatively high affinity for the A(1)AR. as compared to the A(2A)AR, concentration-dependent and selective apparent irreversible binding to the A(1)AR, and ease;of removal of unbound ligand from biological membranes. These :properties indicate that 23b has the potential to be a useful tool for further study of the structure and function of the A(1)AR.

  DOI：

  10.1021/jm000181f