(3-amino-6-phenylpyrazin-2-yl) (Pyrrolidin-1-yl)methanone | 625459-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (3-amino-6-phenylpyrazin-2-yl) (Pyrrolidin-1-yl)methanone
• 英文别名: (3-amino-6-phenylpyrazin-2-yl)-pyrrolidin-1-ylmethanone
• CAS: 625459-35-0
• 化学式: C₁₅H₁₆N₄O
• 分子量: 268.318
• InChiKey: BXTXVXHBYXMGCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-amino-6-phenylpyrazin-2-yl) (Pyrrolidin-1-yl)methanone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到7-hydroxy-2-phenyl-1H-benzoimidazole-4-carboxylic acid amide
  参考文献：
  名称：

  [EN] GLYCOGEN SYNTHASE KINASE 3BETA INHIBITOR, COMPOSITION AND PROCESS FOR THE PREPARATION THEREOF
  [FR] INHIBITEUR DE GLYCOGENE SYNTHASE KINASE 3 DOLLAR G(B), COMPOSITION ET PROCEDE DE PREPARATION ASSOCIE

  摘要：

  具有羟基苯并咪唑羧酰胺的新化合物对抑制糖原合成酶激酶3β（GSK-3β）具有用处。

  公开号：

  WO2004065370A1
• 作为产物：
  描述：

  3-氨基-6-溴吡嗪-2-甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 (3-amino-6-phenylpyrazin-2-yl) (Pyrrolidin-1-yl)methanone
  参考文献：
  名称：

  6-Arylpyrazine-2-carboxamides: A New Core for Trypanosoma brucei Inhibitors

  摘要：

  From a whole-organism high throughput screen of approximately 87000 compounds against Trypanosoma brucei brucei, we recently identified eight new unique compounds for the treatment of human African trypanosomiasis. In an effort to understand the structure activity relationships around these compounds, we report for the first time our results on a new class of trypanocides, the pyrazine carboxamides. Attracted by the low molecular weight (270 g.mol(-1)) of our starting hit (9) and its potency (0.49 mu M), the SAR around the core was explored, leading to compounds having an EC50 as low as 25 nM against T. b. brucei and being more than 1500 times less toxic against mammalian L6 and HEK293 cell lines. The most potent compounds in the series were exquisitely selective for T. brucei over a panel of other protozoan parasites, showing an excellent correlation with the human infective parasite Trypanosoma brucei rhodesiense, the most potent compound (65) having an EC50 of 24 nM. The compounds are highly drug-like and are able to penetrate the CNS, their only limitation currently being their rate of microsomal metabolism. To that effect, efforts to identify potential metabolites of selected compounds are also reported.

  DOI：

  10.1021/acs.jmedchem.5b00438

文献信息

• Protein kinase modulators and methods of use
  申请人：Buhr A. Chris

  公开号：US20060211709A1

  公开（公告）日：2006-09-21

  Substituted aryl 1,4-pyrazine derivatives and their use in treating anxiety disorders, depression and stress related disorders are disclosed.

  本发明揭示了替代芳基1,4-吡嗪衍生物及其在治疗焦虑症、抑郁症和与压力相关的疾病中的应用。
• PROTEIN KINASE MODULATORS AND METHODS OF USE
  申请人：Exelixis, Inc.

  公开号：EP1501514A2

  公开（公告）日：2005-02-02
• EP1501514A4
  申请人：——

  公开号：EP1501514A4

  公开（公告）日：2009-08-26
• US7704995B2
  申请人：——

  公开号：US7704995B2

  公开（公告）日：2010-04-27
• [EN] PROTEIN KINASE MODULATORS AND METHODS OF USE<br/>[FR] MODULATEURS DE PROTEINE KINASE ET PROCEDES D'UTILISATION
  申请人：EXELIXIS INC

  公开号：WO2003093297A2

  公开（公告）日：2003-11-13

  This invention relates to compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion, and to pharmaceutical compositions containing such compounds. Even more specifically, the invention relates to compounds that inhibit, regulate and/or modulate kinases, particularly Checkpoint Kinases, even more particularly Checkpoint Kinase 1, or Chk1. Methods of therapeutically or prophylactically using the compounds and compositions to treat kinase-dependent diseases and conditions are also an aspect of the invention, and include methods of treating cancer, as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, by administering effective amounts of such compounds.