6-Amino-N-benzyl-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxamide | 443103-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-Amino-N-benzyl-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxamide
• 英文别名: 6-amino-N-benzyl-4-(furan-2-yl)pyrazolo[3,4-d]pyrimidine-1-carboxamide
• CAS: 443103-45-5
• 化学式: C₁₇H₁₄N₆O₂
• 分子量: 334.337
• InChiKey: QJFITZRFGJYVRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-Butyl 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate 在 4-二甲氨基吡啶 二甲胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-Amino-N-benzyl-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxamide
  参考文献：
  名称：

  Pyrazolo[3,4-d]pyrimidine derivatives and their use as purinergic receptor antagonists

  摘要：

  使用公式（I）的化合物，其中R1从烷基、烷氧基、芳氧基、烷硫基、芳硫基、芳基、卤素、CN、NR6R7、NR5COR6、NR5CONR6R7、NR5CO2R8和NR5SO2R8中选择；R2从通过不饱和碳连接的杂环芳基中选择；R3从H、烷基、卤素、OR5、SR5和NR6R7中选择；R4从H、非环烷基、CONR6R7、CONR5NR6R7、COR6、CO2R8和SO2R中选择；R5、R6和R7分别从H、烷基和芳基中选择，或者当R6和R7在NR6R7基团中时，R6和R7可以连接形成杂环基团，或者当R5、R6和R7在（CONR5NR6R7）基团中时，R5和R6可以连接形成杂环基团；R8从烷基和芳基中选择，或其在治疗或预防妨碍嘌呤受体，特别是腺苷受体，尤其是A2A受体的紊乱中的使用，可能是有益的，特别是其中所述紊乱是帕金森病等运动紊乱，或所述紊乱是抑郁症、认知或记忆障碍、急性或慢性疼痛、ADHD或嗜睡症，或用于对受试者进行神经保护；公式（I）的化合物用于治疗；以及公式（I）的新化合物本身。

  公开号：

  US20040116447A1

文献信息

• Antagonists of the human adenosine A2A receptor. Part 3: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines and 6-arylpurines
  作者：Roger J. Gillespie、Ian A. Cliffe、Claire E. Dawson、Colin T. Dourish、Suneel Gaur、Allan M. Jordan、Antony R. Knight、Joanne Lerpiniere、Anil Misra、Robert M. Pratt、Jonathan Roffey、Gemma C. Stratton、Rebecca Upton、Scott M. Weiss、Douglas S. Williamson

  DOI：10.1016/j.bmcl.2008.03.072

  日期：2008.5

  A series of pyrazolo[3,4-d]pyrimidine, pyrrolo[2,3-d]pyrimidine and 6-arylpurine adenosine A(2A) antagonists is described. Many examples were highly selective against the human A(1) receptor sub-type and were active in an in vivo model of Parkinson's disease.

  描述了一系列的吡唑并[3,4-d]嘧啶，吡咯并[2,3-d]嘧啶和6-芳基嘌呤腺苷A（2A）拮抗剂。许多示例对人类A（1）受体亚型具有高度选择性，并且在帕金森氏病的体内模型中具有活性。
• PYRAZOLO [3,4-D] PYRIMIDINE DERIVATIVES AND THEIR USE AS PURINERGIC RECEPTOR ANTAGONISTS
  申请人：Gillespie John Roger

  公开号：US20060111373A1

  公开（公告）日：2006-05-25

  Use of a compound of formula (I): wherein R 1 is selected from alkyl, alkoxy, aryloxy, alkylthio, arylthio, aryl, halogen, CN, NR 6 R 7 , NR 5 COR 6 , NR 5 CONR 6 R 7 , NR 5 CO 2 R 8 and NR 5 SO 2 R 8 ; R 2 is selected from heteroaryl attached via an unsaturated carbon; R 3 is selected from H, alkyl, halogen, OR 5 , SR 5 and NR 6 R 7 ; R 4 is selected from H, acyclic alkyl, CONR 6 R 7 , CONR 5 NR 6 R 7 , COR 6 , CO 2 R 8 and SO 2 R 8 ; R 5 , R 6 and R 7 are independently selected from H, alkyl and aryl, or where R 6 and R 7 are in an NR 6 R 7 group, R 6 and R 7 may be linked to form a heterocyclic group, or where R 5 , R 6 and R 7 may be linked to form a heterocyclic group, or where R 5 , R 6 and R 7 are in a (CONR 5 NR 6 R 7 ) group, R 5 and R 6 may be linked to form a heterocyclic group; and R 8 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用公式（I）的化合物：其中R1选择自烷基，烷氧基，芳氧基，烷硫基，芳硫基，芳基，卤素，CN，NR6R7，NR5COR6，NR5CONR6R7，NR5CO2R8和NR5SO2R8; R2选择自通过不饱和碳连接的杂环芳基; R3选择自H，烷基，卤素，OR5，SR5和NR6R7; R4选择自H，非环状烷基，CONR6R7，CONR5NR6R7，COR6，CO2R8和SO2R8; R5，R6和R7独立地选择自H，烷基和芳基，或者当R6和R7在NR6R7组中时，R6和R7可以连接形成杂环基团，或者当R5，R6和R7可以连接形成杂环基团时，或者当R5，R6和R7在（CONR5NR6R7）组中时，R5和R6可以连接形成杂环基团; R8选择自烷基和芳基，或其药学上可接受的盐或前药，在治疗或预防阻断嘌呤受体，特别是腺苷受体，更特别是A2A受体可能有益的紊乱中，特别是其中所述紊乱是运动紊乱，如帕金森病或所述紊乱是抑郁症，认知或记忆障碍，急性或慢性疼痛，ADHD或嗜睡症，或用于在受试者中进行神经保护; 公式（I）的化合物用于治疗; 和公式（I）的新化合物本身。
• Pyrazolo [3,4-d] pyrimidine derivatives and their use as purinergic receptor antagonists
  申请人：Vernalis Research Limited

  公开号：US07629349B2

  公开（公告）日：2009-12-08

  Pharmaceutical compositions and their uses comprising compounds of formula (I): wherein: R1 is selected from: alkyl, alkoxy, aryloxy, alkylthio, arylthio, aryl, halogen, CN, NR6R7, NR5COR6, NR5CONR6R7, NR5CO2R8, and NR5SO2R8; R2 is a heteroaryl attached via an unsaturated ring carbon of said heteroaryl group; R3 is selected from: H, alkyl, halogen, OR5, SR5, and NR6R7; R4 is selected from: H, acyclic alkyl, CONR6R7, CONR5NR6R7, COR6, CO2R8, and SO2R8; R5, R6, and R7 are independently selected from: H, alkyl, and aryl, or where R6 and R7 are in an NR6R7 group, R6 and R7 may be linked to form a hetero cyclic group, or where R5, R6 and R7 are in a (CONR5NR6R7) group, R5 and R6 may be linked to form a heterocyclic group; and R8 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof.

  含有化合物(I)的制药组合物及其用途，其中：R1选自：烷基、烷氧基、芳氧基、烷硫基、芳硫基、芳基、卤素、CN、NR6R7、NR5COR6、NR5CONR6R7、NR5CO2R8和NR5SO2R8；R2是通过其杂环基团的不饱和环碳连接的杂环基；R3选自：H、烷基、卤素、OR5、SR5和NR6R7；R4选自：H、非环状烷基、CONR6R7、CONR5NR6R7、COR6、CO2R8和SO2R8；R5、R6和R7独立地选自：H、烷基和芳基，或者当R6和R7在NR6R7基团中时，R6和R7可以连接形成杂环基团，或者当R5、R6和R7在(CONR5NR6R7)基团中时，R5和R6可以连接形成杂环基团；R8选自烷基和芳基，或其药学上可接受的盐。
• PYRAZOLO 3,4-D]PYRIMIDINE DERIVATIVES AND THEIR USE AS PURINERGIC RECEPTOR ANTAGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1349552A1

  公开（公告）日：2003-10-08
• PYRAZOLO[3,4-d]PYRIMIDINE DERIVATIVES AND THEIR USE AS PURINERGIC RECEPTOR ANTAGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1349552B1

  公开（公告）日：2008-08-20