(E)-8-(3-keto-3-phenyl-1-propen-1-yl)-9-(β-D-ribofuranosyl)adenine

• 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: (E)-8-(3-keto-3-phenyl-1-propen-1-yl)-9-(β-D-ribofuranosyl)adenine
• 英文别名: (E)-3-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]-1-phenylprop-2-en-1-one
• 化学式: C₁₉H₁₉N₅O₅
• 分子量: 397.39
• InChiKey: VRKBZQOPVJHRLW-VFIQZALSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 、 腺苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (E)-8-(3-keto-3-phenyl-1-propen-1-yl)-9-(β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Introduction of alkynyl chains on C-8 of adenosine led to very selective antagonists of the A 3 adenosine receptor

  摘要：

  Some 8-alkynyladenosines were synthesized and evaluated for their adenosine receptor activity, utilizing radioligand binding studies (A(1), A(2A), A(3)) or adenylyl cyclase activity assays (A(2B)). Furthermore, the maximal induction of guanosine 5 '-(gamma -thio)triphosphate ([S-35]GTP gammaS) binding to G proteins and the inhibition of NECA-stimulated binding, in membranes of CHO cells which express the human A(3) receptor, were used to determine the intrinsic activity of these nucleosides at the A(3) adenosine receptor. The results showed that these new adenosine derivatives are very selective ligands for the A(3) receptor subtype and behave as adenosine antagonists, since they do not stimulate basal [S-35]GTP gammaS binding, but inhibit NECA-stimulated binding. This is the first report that adenosine derivatives, with unmodified ribose moiety, are adenosine receptor antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00347-x

文献信息

• Introduction of alkynyl chains on C-8 of adenosine led to very selective antagonists of the A 3 adenosine receptor
  作者：Rosaria Volpini、Stefano Costanzi、Catia Lambertucci、Sauro Vittori、K.-N Klotz、Anna Lorenzen、Gloria Cristalli

  DOI：10.1016/s0960-894x(01)00347-x

  日期：2001.7

  Some 8-alkynyladenosines were synthesized and evaluated for their adenosine receptor activity, utilizing radioligand binding studies (A(1), A(2A), A(3)) or adenylyl cyclase activity assays (A(2B)). Furthermore, the maximal induction of guanosine 5 '-(gamma -thio)triphosphate ([S-35]GTP gammaS) binding to G proteins and the inhibition of NECA-stimulated binding, in membranes of CHO cells which express the human A(3) receptor, were used to determine the intrinsic activity of these nucleosides at the A(3) adenosine receptor. The results showed that these new adenosine derivatives are very selective ligands for the A(3) receptor subtype and behave as adenosine antagonists, since they do not stimulate basal [S-35]GTP gammaS binding, but inhibit NECA-stimulated binding. This is the first report that adenosine derivatives, with unmodified ribose moiety, are adenosine receptor antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.