N-(5-(2-(benzyl(2-(N6-adenosinyl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide | 1068148-10-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-(5-(2-(benzyl(2-(N6-adenosinyl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide
• 英文别名: N-[5-[2-[benzyl-[2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]ethyl]amino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]formamide
• CAS: 1068148-10-6
• 化学式: C₃₅H₃₉N₇O₇
• 分子量: 669.737
• InChiKey: ZXXZBJPTLZXIJA-MFDGMFAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  187
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(5-(2-(benzyl(2-(N6-adenosinyl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以14%的产率得到N-(2-hydroxy-5-((2-(N6-adenosinyl)ethylamino)ethyl)phenyl)formamide
  参考文献：
  名称：

  Synthesis of Bivalent β₂-Adrenergic and Adenosine A₁ Receptor Ligands

  摘要：

  Research in the area of simutaneously targeting more than one G protein-coupled receptor (GPCR) has increased in recent times. By exploiting the cross talk between the beta(2)-adrenergic (beta(2)AR) and adenosine A(1) receptors (A(1)AR) on adenylate cyclase activity, we synthesized a series of bivalent agonists for both GPCRs to generate responses from more than one receptor. We have demonstrated a relationship between the various beta(2)-adrenergic and A(1) adenosine bivalent parameters of linker and bifunctionality by using data that are drawn from in vitro assays. The hexyl-linked 12e (K-i, 311 nM) and butyl-linked 12c (K-i, 863 nM) bivalent compounds displayed reasonable binding affinities for the PAR when compared with the control (-)isoproterenol (K-i, 136 nM), and both compounds also exhibited a persuasive bifunctional trend for both receptors at various drug concentrations. The bivalent compound 12e was also found to have significant EC50 potency (6 nM) at the beta(2)AR in DDT cells.

  DOI：

  10.1021/jm800613s
• 作为产物：
  描述：

  N-(5-(2-((2-aminoethyl)(benzyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide trifluoroacetate 、 6-氯嘌呤核苷 在 N,N-二异丙基乙胺 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以45%的产率得到N-(5-(2-(benzyl(2-(N6-adenosinyl)ethyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide
  参考文献：
  名称：

  Synthesis of Bivalent β₂-Adrenergic and Adenosine A₁ Receptor Ligands

  摘要：

  Research in the area of simutaneously targeting more than one G protein-coupled receptor (GPCR) has increased in recent times. By exploiting the cross talk between the beta(2)-adrenergic (beta(2)AR) and adenosine A(1) receptors (A(1)AR) on adenylate cyclase activity, we synthesized a series of bivalent agonists for both GPCRs to generate responses from more than one receptor. We have demonstrated a relationship between the various beta(2)-adrenergic and A(1) adenosine bivalent parameters of linker and bifunctionality by using data that are drawn from in vitro assays. The hexyl-linked 12e (K-i, 311 nM) and butyl-linked 12c (K-i, 863 nM) bivalent compounds displayed reasonable binding affinities for the PAR when compared with the control (-)isoproterenol (K-i, 136 nM), and both compounds also exhibited a persuasive bifunctional trend for both receptors at various drug concentrations. The bivalent compound 12e was also found to have significant EC50 potency (6 nM) at the beta(2)AR in DDT cells.

  DOI：

  10.1021/jm800613s