furan-3-carboxylic acid N-[4,6-dihydroxy-2-(methylsulfanyl)pyrimidin-5-yl]amide | 884861-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: furan-3-carboxylic acid N-[4,6-dihydroxy-2-(methylsulfanyl)pyrimidin-5-yl]amide
• 英文别名: N-(4-hydroxy-2-methylsulfanyl-6-oxo-1H-pyrimidin-5-yl)furan-3-carboxamide
• CAS: 884861-17-0
• 化学式: C₁₀H₉N₃O₄S
• 分子量: 267.265
• InChiKey: HQWLUMCBEIIROV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  furan-3-carboxylic acid N-[4,6-dihydroxy-2-(methylsulfanyl)pyrimidin-5-yl]amide 在 sodium perborate 、 溶剂黄146 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 22.0h， 生成 7-amino-2-(furan-3-yl)-5-(methylsulfonyl)oxazolo[5,4-d]pyrimidine
  参考文献：
  名称：

  Synthesis and evaluation of 7-amino-2-(2(3)-furyl)-5-phenylethylamino-oxazolo[5,4-d]pyrimidines as potential A2A adenosine receptor antagonists for positron emission tomography (PET)

  摘要：

  The brain A(2A) adenosine receptor (A(2A)AR) participates with the dopamine D, receptor in the control of movement and also might influence behavior. Because PET is an important tool for studying the roles of receptors in disease, a ligand for imaging the brain A(2A)AR is desirable. This report describes the synthesis and A(2A)AR antagonist activities of a panel of phenyl-substituted 7-amino-2-(2-furyl)-5-phenylethylamino-oxazolo [5,4-d]pyrimidines, 11aa-af, and their 3-furyl congeners, 11ba-bd. In competitive binding studies all compounds displaced [H-3]CGS21680 from the A(2A)AR with K-i values of 14-33 nM with selectivity for the A(2A)AR over the A(1)AR of 5- to 94-fold. Autoradiography of brain sections showed a high level of unspecific binding that obscured specific binding. Thus, these compounds are not promising PET ligands. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.018
• 作为产物：
  描述：

  3-糠酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 furan-3-carboxylic acid N-[4,6-dihydroxy-2-(methylsulfanyl)pyrimidin-5-yl]amide
  参考文献：
  名称：

  Synthesis and evaluation of 7-amino-2-(2(3)-furyl)-5-phenylethylamino-oxazolo[5,4-d]pyrimidines as potential A2A adenosine receptor antagonists for positron emission tomography (PET)

  摘要：

  The brain A(2A) adenosine receptor (A(2A)AR) participates with the dopamine D, receptor in the control of movement and also might influence behavior. Because PET is an important tool for studying the roles of receptors in disease, a ligand for imaging the brain A(2A)AR is desirable. This report describes the synthesis and A(2A)AR antagonist activities of a panel of phenyl-substituted 7-amino-2-(2-furyl)-5-phenylethylamino-oxazolo [5,4-d]pyrimidines, 11aa-af, and their 3-furyl congeners, 11ba-bd. In competitive binding studies all compounds displaced [H-3]CGS21680 from the A(2A)AR with K-i values of 14-33 nM with selectivity for the A(2A)AR over the A(1)AR of 5- to 94-fold. Autoradiography of brain sections showed a high level of unspecific binding that obscured specific binding. Thus, these compounds are not promising PET ligands. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.018

文献信息

• Synthesis and evaluation of 7-amino-2-(2(3)-furyl)-5-phenylethylamino-oxazolo[5,4-d]pyrimidines as potential A2A adenosine receptor antagonists for positron emission tomography (PET)
  作者：M HOLSCHBACH、D BIER、S STUSGEN、W WUTZ、W SIHVER、H COENEN、R OLSSON

  DOI：10.1016/j.ejmech.2005.07.018

  日期：2006.1

  The brain A(2A) adenosine receptor (A(2A)AR) participates with the dopamine D, receptor in the control of movement and also might influence behavior. Because PET is an important tool for studying the roles of receptors in disease, a ligand for imaging the brain A(2A)AR is desirable. This report describes the synthesis and A(2A)AR antagonist activities of a panel of phenyl-substituted 7-amino-2-(2-furyl)-5-phenylethylamino-oxazolo [5,4-d]pyrimidines, 11aa-af, and their 3-furyl congeners, 11ba-bd. In competitive binding studies all compounds displaced [H-3]CGS21680 from the A(2A)AR with K-i values of 14-33 nM with selectivity for the A(2A)AR over the A(1)AR of 5- to 94-fold. Autoradiography of brain sections showed a high level of unspecific binding that obscured specific binding. Thus, these compounds are not promising PET ligands. (c) 2005 Elsevier SAS. All rights reserved.