(2S,3S,4R,5R)-5-[2-chloro-6-(cyclopentylamino)purin-9-yl]-3,4-dihydroxy-N,N-dimethylthiolane-2-carboxamide | 1021159-35-2

• 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: (2S,3S,4R,5R)-5-[2-chloro-6-(cyclopentylamino)purin-9-yl]-3,4-dihydroxy-N,N-dimethylthiolane-2-carboxamide
• CAS: 1021159-35-2
• 化学式: C₁₇H₂₃ClN₆O₃S
• 分子量: 426.927
• InChiKey: MZEXKOVEDRMBNG-MEQWQQMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R)-5-[2-chloro-6-(cyclopentylamino)purin-9-yl]-3,4-dihydroxy-N,N-dimethylthiolane-2-carboxamide
  参考文献：
  名称：

  Structure–activity relationships of 2-chloro-N6-substituted-4′-thioadenosine-5′-N,N-dialkyluronamides as human A3 adenosine receptor antagonists

  摘要：

  On the basis of potent and selective A(3) adenosine receptor (AR) antagonist, 2-chloro-N-6-(3-iodobenzyl)-4'-thioadenosine-5'-N,N-dimethyluronamide, structure-activity relationships were studied for a series of 5'-N,N-dialkyluronamide derivatives, synthesized from D-gulonic gamma-lactone. From this study, it was revealed that removal of the hydrogen bond-donating ability of the 5'-uronamide was essential for the pure A(3)AR antagonism. 5'-N,N-Dimethyluronamide derivatives exhibited higher binding affinity than larger 5'-N,N-dialkyl or 5'-N,N-cycloalkylamide derivatives, indicating that steric factors are crucial in binding to the human A(3)AR. A N-6-(3-bromobenzyl) derivative 6c (K-i = 9.32 nM) exhibited the highest binding affinity at the human A3AR with very low binding affinities to other AR subtypes. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.070