2-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine | 443149-41-5

• 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: 2-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine
• 英文别名: 2-chloro-4-(5-chlorothiophen-2-yl)thieno[3,2-d]pyrimidine
• CAS: 443149-41-5
• 化学式: C₁₀H₄Cl₂N₂S₂
• 分子量: 287.193
• InChiKey: NBDHTSGLECSGQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二氯噻吩并[3,2-D]嘧啶 、 碳酸氢钠 、 5-氯噻吩-2-硼酸 在 palladium diacetate 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到2-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine
  参考文献：
  名称：

  Thieno(3,2-d)pyrimidines and furano(3,2-d)pyimidines and their use as purinergic receptor antagonists

  摘要：

  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。

  公开号：

  US20040097524A1

文献信息

• 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：US07384949B2

  公开（公告）日：2008-06-10

  A compound of formula (I), wherein X is S or O; R1 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, COR5, CO2R5, CONR6R7, CONR5NR6R7, NR6R7, NR5CONR6R7, NR5COR6, NR5CO2R8, and NR5SO2R8; R2 is selected from aryl attached via an unsaturated carbon atom; R3 is selected from H, alkyl, hydroxy, alkoxy, halogen, CN and NO2; R4 is selected from H, alkyl, aryl, hydroxy, alkoxy, aryloxy, thioalkyl, thioaryl, halogen, CN, NO2, COR5, CO2R5, CONR6R7, CONR5NR6R7, NR6R7, NR5CONR6R7, NR5COR6, NR5CO2R8 and NR5SO2R8; 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 heterocyclic 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 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 A2A 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(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，CONR6R7，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；R4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受体可能有益的疾病中的使用，特别是其中该疾病是帕金森病等运动障碍，或该疾病是抑郁症、认知或记忆障碍、急性或慢性疼痛、ADHD或嗜睡症，或者该药物是用于对受体进行神经保护的受体。
• 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
• US7384949B2
  申请人：——

  公开号：US7384949B2

  公开（公告）日：2008-06-10
• 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。