3-溴-8-氯-2-甲基咪唑并[1,2-a]吡嗪 | 1124321-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 中文名称: 3-溴-8-氯-2-甲基咪唑并[1,2-a]吡嗪
• 英文名称: 3-bromo-8-chloro-2-methyl-imidazo[1,2-a]pyrazine
• 英文别名: 3-bromo-8-chloro-2-methylimidazo[1,2-a]pyrazine
• CAS: 1124321-36-3
• 化学式: C₇H₅BrClN₃
• 分子量: 246.494
• InChiKey: NRKMUXRBIBCNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-溴-8-氯-2-甲基咪唑并[1,2-a]吡嗪 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 异丁醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 4-[2-methyl-8-[(3-methylsulfonylphenyl)methylamino]imidazo[1,2-a]pyrazin-3-yl]phenol
  参考文献：
  名称：

  Identification of a Series of Compounds with Potent Antiviral Activity for the Treatment of Enterovirus Infections

  摘要：

  Rhinovirus (genus enterovirus) infections are responsible for many of the severe exacerbations of asthma and chronic obstructive pulmonary disease. Other members of the genus can cause life-threatening acute neurological infections. There is currently no antiviral drug approved for the treatment of such infections. We have identified a series of potent, broad-spectrum antiviral compounds that inhibit the replication of the human rhinovirus, Coxsackie virus, poliovirus, and enterovirus-71. The mechanism of action of the compounds has been established as inhibition of a lipid kinase, PI4KIII beta. Inhibition of hepatitis C replication in a replicon assay correlated with enterovirus inhibition.

  DOI：

  10.1021/ml400095m
• 作为产物：
  描述：

  8-氯-2-甲基咪唑并[1,2-a]吡嗪 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到3-溴-8-氯-2-甲基咪唑并[1,2-a]吡嗪
  参考文献：
  名称：

  潜在，选择性和口服活性磷酸二酯酶10A抑制剂的潜在治疗精神分裂症的发现。

  摘要：

  我们报告发现了一系列的咪唑并[1,2- a ]吡嗪衍生物作为磷酸二酯酶10A（PDE10A）的新型抑制剂。在高通量筛选活动中，我们鉴定了咪唑并吡嗪衍生物1，一种相对于其他磷酸二酯酶（PDE）具有有限选择性的PDE10A抑制剂。随后的研究1和由（甲氧基乙基）吡唑部分取代三甲氧基苯基保持PDE10A抑制，但提高了对其他PDE的选择性。对结构-活动和结构-财产关系的系统检查和分析导致发现2，一种体外有效和选择性的PDE10A抑制剂，具有较高的PDE10A纹状体占有率，有望在不同的精神分裂症啮齿动物行为模型中发挥体内功效，并在大鼠中具有良好的药代动力学特征。

  DOI：

  10.1021/jm500073h

文献信息

• [EN] IMIDAZO [1, 2 -A] PYRAZINE DERIVATIVES AND THEIR USE FOR THE PREVENTION OR TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND METABOLIC DISORDERS AND DISEASES<br/>[FR] DÉRIVÉS D'IMIDAZO[1,2-A]PYRAZINE ET LEUR UTILISATION POUR LA PRÉVENTION OU LE TRAITEMENT DE TROUBLES ET MALADIES NEUROLOGIQUES, PSYCHIATRIQUES ET MÉTABOLIQUES.
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011110545A1

  公开（公告）日：2011-09-15

  The present invention relates to novel imidazo[1,2-a]pyrazine derivatives which are inhibitors of the phosphodiesterase 10 enzyme (PDE10) and which are useful for the treatment or prevention of neurological, psychiatric and metabolic disorders in which the PDE10 enzyme is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, to the use of such compounds or pharmaceutical compositions for the prevention or treatment of neurological, psychiatric and metabolic disorders and diseases.

  本发明涉及新型咪唑并[1,2-a]吡嗪衍生物，它们是磷酸二酯酶10（PDE10）的抑制剂，并且对涉及PDE10酶的神经、精神和代谢性疾病的治疗或预防具有用处。该发明还涉及包含这类化合物的药物组合物，用于制备这类化合物和组合物的方法，以及利用这类化合物或药物组合物预防或治疗神经、精神和代谢性疾病和疾病。
• IMIDAZO[1,2-a]PYRAZINE DERIVATIVES AND THEIR USE FOR THE PREVENTION OR TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND METABOLIC DISORDERS AND DISEASES
  申请人：Bartolomé-Nebreda José Manuel

  公开号：US20120329792A1

  公开（公告）日：2012-12-27

  The present invention relates to novel imidazo[1,2-a]pyrazine derivatives which are inhibitors of the phosphodiesterase 10 enzyme (PDE10) and which are useful for the treatment or prevention of neurological, psychiatric and metabolic disorders in which the PDE10 enzyme is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, to the use of such compounds or pharmaceutical compositions for the prevention or treatment of neurological, psychiatric and metabolic disorders and diseases.

  本发明涉及新型咪唑并[1,2-a]吡嗪衍生物，其为磷酸二酯酶10（PDE10）的抑制剂，并且适用于治疗或预防涉及PDE10酶的神经、精神和代谢性疾病。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物或药物组合物预防或治疗神经、精神和代谢性疾病和疾病。
• IMIDAZOPYRAZINE COMPOUNDS
  申请人：Macleod Angus

  公开号：US20110166147A1

  公开（公告）日：2011-07-07

  Novel imidazopyrazine compounds are disclosed that have a formula represented by the following: Formula (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a viral infection, in particular a HCV, HRV, Sb and/or CVB in a patient in need thereof.

  本发明揭示了一种具有以下公式（I）所表示的化学式的新型咪唑吡唑化合物。该化合物可制备成药物组合物，并可用于预防和治疗病人中的病毒感染，特别是HCV、HRV、Sb和/或CVB。
• Substituted imidazo[1,2-a]pyrazine compounds useful for the treatment of viral infections
  申请人：MacLeod Angus

  公开号：US08362018B2

  公开（公告）日：2013-01-29

  Novel imidazopyrazine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a viral infection, in particular a HCV, HRV, Sb and/or CVB in a patient in need thereof.

  本发明涉及新型咪唑吡嗪化合物，其化学式如下：所述化合物可制备为药物组合物，并可用于预防和治疗病毒感染，特别是治疗HCV、HRV、Sb和/或CVB等病毒感染的患者。
• Imidazo[1,2-a]pyrazine compounds for treatment of viral infections such as hepatitis
  申请人：Biofocus DPI Limited

  公开号：EP2567960A2

  公开（公告）日：2013-03-13

  Novel imidazopyrazine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a viral infection, in particular a HCV, HRV, Sb and/or CVB in a patient in need thereof.

  本发明公开了新型咪唑吡嗪化合物，其分子式如下： 这些化合物可制备成药物组合物，并可用于预防和治疗病毒感染，特别是有需要的患者的 HCV、HRV、Sb 和/或 CVB。