2-(3-溴-1H-1,2,4-噻唑)吡啶 | 550363-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(3-溴-1H-1,2,4-噻唑)吡啶
• 英文名称: 2-(3-bromo-1H-1,2,4-triazol-1-yl)pyridine
• 英文别名: 2-(3-bromo-1,2,4-triazol-1-yl)pyridine
• CAS: 550363-95-6
• 化学式: C₇H₅BrN₄
• 分子量: 225.047
• InChiKey: MJSLJIWJMXUAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氰基苯硼酸 、 2-(3-溴-1H-1,2,4-噻唑)吡啶 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 以54%的产率得到3-(1-Pyridin-2-yl-1H-[1,2,4]triazol-3-yl)-benzonitrile
  参考文献：
  名称：

  Discovery of Novel Heteroarylazoles That Are Metabotropic Glutamate Subtype 5 Receptor Antagonists with Anxiolytic Activity

  摘要：

  The highly potent, selective, and brain-penetrant metabotropic glutamate subtype 5 (mGlu5) receptor antagonists 3-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (47) and 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (48) are reported. Compound 47 is active in the rat fear-potentiated startle (FPS) model of anxiety with ED50 = 5.4 mg/kg (po) when dosed acutely. In this model the anxiolytic effects of 47 rapidly tolerate on repeated dosing.

  DOI：

  10.1021/jm049828c
• 作为产物：
  描述：

  3-溴-1H-1,2,4-噻唑 、 三氟甲磺酸N-吡啶鎓 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以20%的产率得到2-(3-溴-1H-1,2,4-噻唑)吡啶
  参考文献：
  名称：

  Discovery of Novel Heteroarylazoles That Are Metabotropic Glutamate Subtype 5 Receptor Antagonists with Anxiolytic Activity

  摘要：

  The highly potent, selective, and brain-penetrant metabotropic glutamate subtype 5 (mGlu5) receptor antagonists 3-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (47) and 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (48) are reported. Compound 47 is active in the rat fear-potentiated startle (FPS) model of anxiety with ED50 = 5.4 mg/kg (po) when dosed acutely. In this model the anxiolytic effects of 47 rapidly tolerate on repeated dosing.

  DOI：

  10.1021/jm049828c

文献信息

• Heteroaryl substituted triazole modulators of metabotropic glutamate receptor-5
  申请人：Cosford D.P. Nicholas

  公开号：US20050020585A1

  公开（公告）日：2005-01-27

  Triazole compounds substituted directly, or by a bridge, with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl which are metabotropic glutamate receptor—subtype 5 (“mGluR5”) modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other diseases.

  直接或通过桥连基取代的三唑化合物，其杂环芳基团含有与杂环芳基连接点相邻的N，可作为代谢型谷氨酸受体亚型5（“mGluR5”）调节剂，用于治疗精神和情绪障碍，例如精神分裂症、焦虑症、抑郁症、双相障碍和惊恐症，以及用于治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、药物戒断和其他疾病。
• HETEROARYL SUBSTITUTED TRIAZOLE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5
  申请人：Merck & Co., Inc.

  公开号：EP1458708A2

  公开（公告）日：2004-09-22
• EP1458708A4
  申请人：——

  公开号：EP1458708A4

  公开（公告）日：2005-11-16
• US7105548B2
  申请人：——

  公开号：US7105548B2

  公开（公告）日：2006-09-12
• [EN] HETEROARYL SUBSTITUTED TRIAZOLE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] MODULATEURS TRIAZOLE SUBSTITUES PAR HETEROARYLE DU RECEPTEUR METABOTROPIQUE 5 DU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2003051315A2

  公开（公告）日：2003-06-26

  Triazole compounds substituted directly, or by a bridge, with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl which are metabotropic glutamate receptor - subtype 5 ('mGluR5') modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other diseases.