| 1383554-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• CAS: 1383554-86-6
• 化学式: C₃₀H₂₈ClN₅O₂
• 分子量: 526.038
• InChiKey: JCRVQZAWFBVQRB-LQEJYONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  74.09
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 三氟甲磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (1R,2R,3S,4R,5S)-4-(2-((2-chlorophenyl)ethynyl)-6-(2-phenylethylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
  参考文献：
  名称：

  Truncated Nucleosides as A₃ Adenosine Receptor Ligands: Combined 2-Arylethynyl and Bicyclohexane Substitutions

  摘要：

  C2-Arylethynyladenosine-5'-N-methyluronamides containing a bicyclo[3.1.0]hexane [(N)-methanocarba] ring are selective A(3) adenosine receptor (AR) agonists. Similar 4'-truncated C2-arylethynyl-(N)-methanocarba nucleosides containing alkyl or alkylaryl groups at the N-6 position were low-efficacy agonists or antagonists of the human A(3)AR with high selectivity. Higher hA(3)AR affinity was associated with N-6-methyl and ethyl (K-i = 3-6 nM) than with N-6-arylallcyl groups. However, combined C2-phenylethynyl and N-6-2-phenylethyl substitutions in selective antagonist 15 provided a K-i of 20 nM. Differences between 4'-truncated and nontruncated analogues of extended C2-p-biphenylethynyl substitution suggested a ligand reorientation in AR binding, dominated by bulky N-6 groups in analogues lacking a stabilizing S'-uronamide moiety. Thus, 4'-truncation of C2-arylethynyl-(N)-methanocarba adenosine derivatives is compatible with general preservation of A(3)AR selectivity, especially with small N-6 groups, but reduced efficacy in A(3)AR-induced inhibition of adenylate cyclase.

  DOI：

  10.1021/ml300107e
• 作为产物：
  描述：

  2-苯乙胺盐酸盐 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Truncated Nucleosides as A₃ Adenosine Receptor Ligands: Combined 2-Arylethynyl and Bicyclohexane Substitutions

  摘要：

  C2-Arylethynyladenosine-5'-N-methyluronamides containing a bicyclo[3.1.0]hexane [(N)-methanocarba] ring are selective A(3) adenosine receptor (AR) agonists. Similar 4'-truncated C2-arylethynyl-(N)-methanocarba nucleosides containing alkyl or alkylaryl groups at the N-6 position were low-efficacy agonists or antagonists of the human A(3)AR with high selectivity. Higher hA(3)AR affinity was associated with N-6-methyl and ethyl (K-i = 3-6 nM) than with N-6-arylallcyl groups. However, combined C2-phenylethynyl and N-6-2-phenylethyl substitutions in selective antagonist 15 provided a K-i of 20 nM. Differences between 4'-truncated and nontruncated analogues of extended C2-p-biphenylethynyl substitution suggested a ligand reorientation in AR binding, dominated by bulky N-6 groups in analogues lacking a stabilizing S'-uronamide moiety. Thus, 4'-truncation of C2-arylethynyl-(N)-methanocarba adenosine derivatives is compatible with general preservation of A(3)AR selectivity, especially with small N-6 groups, but reduced efficacy in A(3)AR-induced inhibition of adenylate cyclase.

  DOI：

  10.1021/ml300107e