4'-(2-呋喃基)-[4,5'-联嘧啶]-2'-胺 | 851371-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4'-(2-呋喃基)-[4,5'-联嘧啶]-2'-胺
• 英文名称: 4'-(2-furyl)-4,5'-bipyrimidin-2'-amine
• 英文别名: 4'-(Furan-2-yl)-[4,5'-bipyrimidin]-2'-amine；4-(furan-2-yl)-5-pyrimidin-4-ylpyrimidin-2-amine
• CAS: 851371-58-9
• 化学式: C₁₂H₉N₅O
• 分子量: 239.236
• InChiKey: QGQIVJFMLHWCGD-UHFFFAOYSA-N

物化性质

• 熔点：
  222℃
• 密度：
  1.344

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-(2-呋喃基)-[4,5'-联嘧啶]-2'-胺 在 copper(l) iodide 氢溴酸 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 28.0h， 生成 5-{[4'-(2-furyl)-4,5'-bipyrimidin-2'-yl]amino}pyridin-2(1H)-one
  参考文献：
  名称：

  Discovery and Characterization of 4‘-(2-Furyl)-N-pyridin-3-yl-4,5‘-bipyrimidin-2‘-amine (LAS38096), a Potent, Selective, and Efficacious A_2B Adenosine Receptor Antagonist

  摘要：

  A novel series of N-heteroaryl 4'-(2-furyl)-4,5'-bipyrimidin-2'-amines has been identified as potent and selective A(2B) adenosine receptor antagonists. In particular, compound 5 showed high affinity for the A(2B) receptor (K-i = 17 nM), good selectivity (IC50: A(1) > 1000 nM, A(2A) > 2500 nM, A(3) > 1000 nM), displayed a favorable pharmacokinetic profile in preclinical species, and showed efficacy in functional in vitro models.

  DOI：

  10.1021/jm061333v
• 作为产物：
  描述：

  4-甲基嘧啶 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4'-(2-呋喃基)-[4,5'-联嘧啶]-2'-胺
  参考文献：
  名称：

  Discovery and Characterization of 4‘-(2-Furyl)-N-pyridin-3-yl-4,5‘-bipyrimidin-2‘-amine (LAS38096), a Potent, Selective, and Efficacious A_2B Adenosine Receptor Antagonist

  摘要：

  A novel series of N-heteroaryl 4'-(2-furyl)-4,5'-bipyrimidin-2'-amines has been identified as potent and selective A(2B) adenosine receptor antagonists. In particular, compound 5 showed high affinity for the A(2B) receptor (K-i = 17 nM), good selectivity (IC50: A(1) > 1000 nM, A(2A) > 2500 nM, A(3) > 1000 nM), displayed a favorable pharmacokinetic profile in preclinical species, and showed efficacy in functional in vitro models.

  DOI：

  10.1021/jm061333v

文献信息

• Discovery of N-(5,6-diarylpyridin-2-yl)amide derivatives as potent and selective A2B adenosine receptor antagonists
  作者：Paul Eastwood、Jacob Gonzalez、Sergio Paredes、Arsenio Nueda、Teresa Domenech、Joan Alberti、Bernat Vidal

  DOI：10.1016/j.bmcl.2010.01.045

  日期：2010.3

  The synthesis and SAR of a series of N-(5,6-diarylpyridin-2-yl)amide derivatives as potent A2B adenosine receptor antagonists is described. Several compounds showed good selectivity versus other adenosine receptors. The potent and selective analogue 9 was shown to have good oral bioavailability in the rat.

  描述了作为有效的A 2B腺苷受体拮抗剂的一系列N-（5,6-二芳基吡啶-2-基）酰胺衍生物的合成和SAR 。与其他腺苷受体相比，几种化合物具有良好的选择性。强有力的和选择性的类似物9被证明在大鼠中具有良好的口服生物利用度。
• [EN] PYRIMIDIN-2-AMINE DERIVATES AND THEIR USE AS A2B ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE PYRIMIDIN-2-AMINE ET UTILISATION DE CEUX-CI EN TANT QU'ANTAGONISTES DU RECEPTEUR DE L'ADENOSINE A2B
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2005040155A1

  公开（公告）日：2005-05-06

  This invention is directed to new potent and selective antagonists of the A2B adenosine receptor having the general formula (I) to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  本发明涉及新型强效选择性A2B腺苷受体拮抗剂，其具有一般式(I)，以及其制备方法；涉及包含它们的药物组合物；以及它们在治疗中的应用。
• Pyrimidin-2-Amine Derivatives and Their Use as A2b Adenosine Receptor Antagonists
  申请人：Vidal Juan Bernat

  公开号：US20070265273A1

  公开（公告）日：2007-11-15

  This invention is directed to new potent and selective antagonists of the A 2B adenosine receptor having the general formula (I); to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  本发明涉及一种新型的A2B腺苷受体具有一般式(I)的高效选择性拮抗剂，以及它们的制备方法、包含它们的药物组合物和它们在治疗中的应用。
• PYRIMIDIN-2-AMINE DERIVATIVES AND THEIR USE AS A2B ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Almirall Prodesfarma, S.A.

  公开号：EP1668000A1

  公开（公告）日：2006-06-14