5-amino-2-methylthiopyrimidine-4,6-diol | 884861-16-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-amino-2-methylthiopyrimidine-4,6-diol
• 英文别名: 5-amino-2-(methylsulfanyl)pyrimidine-4,6-diol；5-amino-4-hydroxy-2-methylsulfanyl-1H-pyrimidin-6-one
• CAS: 884861-16-9
• 化学式: C₅H₇N₃O₂S
• mdl: MFCD18459183
• 分子量: 173.195
• InChiKey: SJUBVFWOTVLTGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-2-methylthiopyrimidine-4,6-diol 在 sodium perborate 、 sodium hydroxide 、 溶剂黄146 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 23.0h， 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：

  5-amino-2-mercaptopyrimidine-4,6-diol 以73%的产率得到
  参考文献：
  名称：

  HARNDEN, MICHAEL R.;HURST, DEREK T., AUSTRAL. J. CHEM., 43,(1990) N, C. 55-62

  摘要：

  DOI：

文献信息

• Harnden, Michael R.; Hurst, Derek T., Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 55 - 62
  作者：Harnden, Michael R.、Hurst, Derek T.

  DOI：——

  日期：——
• HARNDEN, MICHAEL R.;HURST, DEREK T., AUSTRAL. J. CHEM., 43,(1990) N, C. 55-62
  作者：HARNDEN, MICHAEL R.、HURST, DEREK T.

  DOI：——

  日期：——
• 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.