8-chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazine | 887475-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazine
• 英文别名: 8-Chloro-2-(3-methoxy-phenyl)-imidazo[1,2-a]pyrazine
• CAS: 887475-68-5
• 化学式: C₁₃H₁₀ClN₃O
• 分子量: 259.695
• InChiKey: XZBHHWUQNPMQEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以61%的产率得到2-(3-methoxyphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationship Studies of Novel Fused Heterocycles-Linked Triazoles with Good Activity and Water Solubility

  摘要：

  Triazoles with fused-heterocycle nuclei were designed and evaluated for their in vitro activity on the basis of the binding mode of albaconazole using molecular docking, along with SAR of antifungal triazoles. Tetrahydro-[1,2,4]-triazolo[1,5-a]pyrazine and tetrahydro-thiazolo[5,4-c]pyridine nuclei were preferable to the other four fused-heterocycle nuclei investigated. Potent in vitro activity, broad spectrum and better water solubility were attained when triazoles containing nitrogen aromatic heterocycles were attached to these two nuclei. The most potent compounds 27aa and 45x, with low hERG inhibition and hepatocyte toxicity, both exhibited excellent activity against Candida, Cryptococcus, and Aspergillus spp., as well as selected fluconazole-resistant strains. A high water-soluble compound 58 (the disulfate salt of 45x) displayed unsatisfactory in vivo activity because of its poor PK profiles. Mice infected with C.alb. SC5314 and C.alb. 103 (fluconazole-resistant strain) and administered with 27aa displayed significantly improved survival rates. 27aa also showed favorable pharmacokinetic (PK) profiles.

  DOI：

  10.1021/jm4016284
• 作为产物：
  描述：

  2-氯-3-氨基吡嗪 、 2-溴-3‘-甲氧基苯乙酮 在 Isopropanol methylene chloride 、 sodium hydroxide 、 Brine 、 Sodium sulfate-III 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以afforded 8-chloro-2-(3-methoxy-phenyl)-imidazo[1,2-a]pyrazine (76 mg, 19%)的产率得到8-chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyrazine
  参考文献：
  名称：

  Novel imidazopyrazines as cyclin dependent kinase inhibitors

  摘要：

  在其多种实施方式中，本发明提供了一种新型的咪唑[1,2-a]吡嗪化合物作为细胞周期蛋白依赖性激酶的抑制剂，制备这种化合物的方法，含有一种或多种这样的化合物的制药组合物，制备包含一种或多种这样的化合物的制药配方的方法，以及使用这种化合物或制药组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。

  公开号：

  US20060106023A1

文献信息

• Imidazopyrazines as protein kinase inhibitors
  申请人：Zhao Lianyun

  公开号：US20070117804A1

  公开（公告）日：2007-05-24

  In its many embodiments, the present invention provides a novel class of imidazopyrazine compounds as inhibitors of protein and/or checkpoint kinases, methods of preparing such compounds, pharmaceutical compositions including one or more such compounds, methods of preparing pharmaceutical formulations including one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the protein or checkpoint kinases using such compounds or pharmaceutical compositions.

  本发明的多种实施例提供了一类新型的咪唑吡嗪化合物，作为蛋白质和/或检查点激酶的抑制剂，包括制备这类化合物的方法、包含一个或多个这类化合物的药物组合物、制备包含一个或多个这类化合物的药物制剂的方法，以及使用这类化合物或药物组合物治疗、预防、抑制或改善与蛋白质或检查点激酶相关的一个或多个疾病的方法。
• Methods for inhibiting protein kinases
  申请人：Guzi J. Timothy

  公开号：US20070105864A1

  公开（公告）日：2007-05-10

  The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim-1 kinase, and tyrosine kinase using imidazo[1,2-a]pyrazine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.

  本发明提供了利用咪唑并[1,2-a]吡嗪化合物抑制来自AKT、检查点激酶、枢纽激酶、Pim-1激酶和酪氨酸激酶的蛋白激酶的方法，以及利用这些化合物治疗、预防、抑制或改善与蛋白激酶相关的一种或多种疾病的方法。
• Novel imidazopyrazines as cyclin dependent kinase inhibitors
  申请人：Guzi J. Timothy

  公开号：US20060106023A1

  公开（公告）日：2006-05-18

  In its many embodiments, the present invention provides a novel class of imidazo[1,2-a]pyrazine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一种新型的咪唑[1,2-a]吡嗪化合物作为细胞周期蛋白依赖性激酶的抑制剂，制备这种化合物的方法，含有一种或多种这样的化合物的制药组合物，制备包含一种或多种这样的化合物的制药配方的方法，以及使用这种化合物或制药组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。
• Imidazopyrazines as cyclin dependent kinase inhibitors
  申请人：Schering Corporation

  公开号：US07576085B2

  公开（公告）日：2009-08-18

  In its many embodiments, the present invention provides a novel class of imidazo[1,2-a]pyrazine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions. An illustrative compound of the invention is shown below:

  在其多种实施形式中，本发明提供了一种新型的咪唑并[1,2-a]吡嗪化合物，作为细胞周期蛋白依赖性激酶的抑制剂，制备这种化合物的方法，含有一种或多种这种化合物的制药组合物，制备包含一种或多种这种化合物的制药配方的方法，以及使用这种化合物或制药组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。下面是本发明的一个示例化合物：
• METHODS FOR INHIBITING PROTEIN KINASES
  申请人：Schering Corporation

  公开号：EP1945216A1

  公开（公告）日：2008-07-23