N-(2-hydroxyethyl)-4-(2-thiazolyl)thieno[3,2-d]pyrimidine-2-amine | 443148-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: N-(2-hydroxyethyl)-4-(2-thiazolyl)thieno[3,2-d]pyrimidine-2-amine
• 英文别名: 2-[[4-(1,3-Thiazol-2-yl)thieno[3,2-d]pyrimidin-2-yl]amino]ethanol
• CAS: 443148-19-4
• 化学式: C₁₁H₁₀N₄OS₂
• 分子量: 278.359
• InChiKey: CAQGMMDINLWTBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-Chloro-4-(2-thiazolyl)thieno[3,2-d]pyrimidine 、 C.I.酸性橙108 生成 N-(2-hydroxyethyl)-4-(2-thiazolyl)thieno[3,2-d]pyrimidine-2-amine
  参考文献：
  名称：

  Antagonists of the human adenosine A2A receptor. Part 2: Design and synthesis of 4-arylthieno[3,2-d]pyrimidine derivatives

  摘要：

  We describe herein the discovery and development of a series of 4-arylthieno[3,2-d]pyrimidines which are potent adenosine A(2A) receptor antagonists. These novel compounds show high degrees of selectivity against the human A(1), A(2B) and A(3) receptor sub-types. Moreover, a number of these compounds show promising activity in vivo, suggesting potential utility in the treatment of Parkinson's disease. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.076

文献信息

• Thieno(3,2-d)pyrimidines and furano(3,2-d)pyimidines and their use as purinergic receptor antagonists
  申请人：——

  公开号：US20040097524A1

  公开（公告）日：2004-05-20

  A compound of formula (I), wherein X is S or O; R 1 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, COR 5 , CO 2 R 5 , CONR 6 R 7 , CONR 5 NR 6 R 7 , NR 6 R 7 , NR 5 CONR 6 R 7 , NR 5 COR 6 , NR 5 CO 2 R 8 , and NR 5 SO 2 R 8 ; R 2 is selected from aryl attached via an unsaturated carbon atom; R 3 is selected from H, alkyl, hydroxy, alkoxy, halogen, CN and NO 2 ; R 4 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, NO 2 , COR 5 , CO 2 R 5 , CONR 6 R 7 , CONR 5 NR 6 R 7 , NR 6 R 7 , NR 5 CONR 6 R 7 , NR 5 COR 6 , NR 5 CO 2 R 8 and NR 5 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 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, and the use thereof in therapy and 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 a Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or wherein said medicament is for neuroprotection in a subject. 1

  式（I）的化合物，其中X为S或O；R1选择自H，烷基，芳基，羟基，烷氧基，芳氧基，硫代烷基，硫代芳基，卤素，CN，COR5，CO2R5，CONR6R7，CONR5NR6R7，NR6R7，NR5CONR6R7，NR5COR6，NR5CO2R8和NR5SO2R8；R2选择自通过不饱和碳原子连接的芳基；R3选择自H，烷基，羟基，烷氧基，卤素，CN和NO2；R4选择自H，烷基，芳基，羟基，烷氧基，芳氧基，硫代烷基，硫代芳基，卤素，CN，NO2，COR5，CO2R5，CONR6R7，CONR5NR6R7，NR6R7，NR5CONR6R7，NR5COR6，NR5CO2R8和NR5SO2R8；R5，R6和R7独立选择自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选择自烷基和芳基，或其在治疗中的药用盐或前药，以及其在治疗或预防阻断嘌呤受体，特别是腺苷受体，尤其是A2A受体可能有益的紊乱中的使用，特别是其中所述紊乱是帕金森病等运动障碍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，或者其中所述药物是用于受试者的神经保护。
• Thieno(3,2-d)pyrimidines and furano(3,2-d)pyramidines and their use as purinergic receptor antagonists
  申请人：Gillespie Roger John

  公开号：US20080153820A1

  公开（公告）日：2008-06-26

  A compound of formula (I), wherein X is S or O; R 1 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, COR 5 , CO 2 R 5 , CONR 5 R 7 , CONR 5 NR 6 R 7 , NR 6 R 7 , NR 5 CONR 6 R 7 , NR 5 COR 6 , NR 5 CO 2 R 8 , and NR 5 SO 2 R 8 ; R 2 is selected from aryl attached via an unsaturated carbon atom; R 3 is selected from H, alkyl, hydroxy, alkoxy, halogen, CN and NO 2 ; R 3 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, NO 2 , COR 5 , CO 2 R 5 , CONR 6 R 7 , CONR 5 NR 6 R 7 , NR 6 R 7 , NR 5 CONR 6 R 7 , NR 5 COR 6 , NR 5 CO 2 R 8 and NR 5 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 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, and the use thereof in therapy and 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 a Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or wherein said medicament is for neuroprotection in a subject.

  化合物的化学式为(I)，其中X为S或O; R1选自H、烷基、芳基、羟基、烷氧基、芳氧基、硫代烷基、硫代芳基、卤素、CN、COR5、CO2R5、CONR5R7、CONR5NR6R7、NR6R7、NR5CONR6R7、NR5COR6、NR5CO2R8和NR5SO2R8; R2选自通过不饱和碳原子连接的芳基; R3选自H、烷基、羟基、烷氧基、卤素、CN和NO2; R3选自H、烷基、芳基、羟基、烷氧基、芳氧基、硫代烷基、硫代芳基、卤素、CN、NO2、COR5、CO2R5、CONR6R7、CONR5NR6R7、NR6R7、NR5CONR6R7、NR5COR6、NR5CO2R8和NR5SO2R8; R5、R6和R7分别选自H、烷基和芳基，或者其中R6和R7在(NR6R7)基团中，R6和R7可以连接形成杂环基团，或者其中R5、R6和R7在(CONR5NR6R7)基团中，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或前药，以及在治疗和治疗阻断嘌呤受体，特别是腺苷受体，尤其是A2A受体可能有益的紊乱的使用，特别是其中该紊乱是运动紊乱，如帕金森病或该紊乱是抑郁症、认知或记忆障碍、急性或慢性疼痛、ADHD或嗜睡症，或者其中该药物是用于对受试者进行神经保护。
• THIENO(3,2-d)PYRIMIDINES AND FURANO(3,2-d)PYRIMIDINES AND THEIR USE AS PURINERGIC RECEPTOR ANTAGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1349861B1

  公开（公告）日：2008-09-10
• METHODS AND COMPOSITIONS FOR IMPROVING IMMUNE RESPONSES
  申请人：Sitkovsky Michail V.

  公开号：US20100178299A1

  公开（公告）日：2010-07-15

  The present invention relates to compositions and methods for enhancing an immune response, for example to a vaccine, by combining the administration of oxygen (O 2 gas), an adenosine pathway antagonist and/or an HIF-1α antagonist, and/or inhibitors of enzymes that produce or generate adenosine with the administration of the vaccine to the patient. The present invention also relates to methods of inducing or enhancing immune responses, methods of treating subjects having a tumor, methods of ablating or killing tumor cells and methods of disrupting the blood supply to a tumor, comprising administering oxygen alone or in combination with therapeutic agents that prevent inhibition of anti-tumor T cells. Tumor defense-resistant immune cells, anti-viral immune cells, and methods of their production are also disclosed.
• US7384949B2
  申请人：——

  公开号：US7384949B2

  公开（公告）日：2008-06-10