2-(2-phenylethylamino)-6-chloropyrazine | 874143-68-7

• 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: 2-(2-phenylethylamino)-6-chloropyrazine
• 英文别名: 6-Chloro-N-(2-phenylethyl)-2-pyrazinamine；6-chloro-N-(2-phenylethyl)pyrazin-2-amine
• CAS: 874143-68-7
• 化学式: C₁₂H₁₂ClN₃
• mdl: MFCD16041667
• 分子量: 233.7
• InChiKey: IJZLEHMAAMJSMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-phenylethylamino)-6-chloropyrazine 、 3-乙酰胺基苯硼酸 在 PdCl₂[1,3-bis(diphenylphosphino)propane]*CH₂Cl₂ 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 4.0h， 以67.6%的产率得到N-[3-(6-Phenethylamino-pyrazin-2-yl)-phenyl]-acetamide
  参考文献：
  名称：

  Novel Inhibitors of B-RAF Based on a Disubstituted Pyrazine Scaffold. Generation of a Nanomolar Lead

  摘要：

  B-RAF, a serine/threonine kinase, plays an important role in the development of certain classes of cancer, especially melanoma. As a result of high-throughput screening of a 23,000 compound library, 2-(3,4,5-trimethoxyphenylamino)-6-(3-acetamidophenyl)pyrazine, 1, was identified as a low micromolar (IC50 = 3.5 mu M) B-RAF inhibitor. This compound was chosen as the starting point of a program aimed at producing potent inhibitors of B-RAF. We have synthesized a series of 40 novel compounds, which involved extensive modifications to the 2-(3,4,5-trimethoxyphenylamino) moiety (ring A) of 1. Their biological profiles against isolated B-RAF and mutated B-RAF in a cellular assay have been determined. These efforts led to the identification of two compounds exhibiting activities lower than 800 nM against B-RAF.

  DOI：

  10.1021/jm050983g
• 作为产物：
  描述：

  2,6-二氯吡嗪 、 2-苯乙胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以53.4%的产率得到2-(2-phenylethylamino)-6-chloropyrazine
  参考文献：
  名称：

  Novel Inhibitors of B-RAF Based on a Disubstituted Pyrazine Scaffold. Generation of a Nanomolar Lead

  摘要：

  B-RAF, a serine/threonine kinase, plays an important role in the development of certain classes of cancer, especially melanoma. As a result of high-throughput screening of a 23,000 compound library, 2-(3,4,5-trimethoxyphenylamino)-6-(3-acetamidophenyl)pyrazine, 1, was identified as a low micromolar (IC50 = 3.5 mu M) B-RAF inhibitor. This compound was chosen as the starting point of a program aimed at producing potent inhibitors of B-RAF. We have synthesized a series of 40 novel compounds, which involved extensive modifications to the 2-(3,4,5-trimethoxyphenylamino) moiety (ring A) of 1. Their biological profiles against isolated B-RAF and mutated B-RAF in a cellular assay have been determined. These efforts led to the identification of two compounds exhibiting activities lower than 800 nM against B-RAF.

  DOI：

  10.1021/jm050983g

文献信息

• [EN] RHODANINES AND RELATED HETEROCYCLES AS KINASE INHIBITORS<br/>[FR] RHODANINES ET HÉTÉROCYCLES ASSOCIÉS EN TANT QU'INHIBITEURS DE KINASE
  申请人：CYLENE PHARMACEUTICALS INC

  公开号：WO2010148351A1

  公开（公告）日：2010-12-23

  The invention provides compounds that inhibit PIM kinases and/or CK2, and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, vascular disorders, pathogenic infections and certain immunological disorders.