6-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪 | 240815-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 中文名称: 6-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪
• 英文名称: 6-chloroimidazo[1,5-a]pyrido[3,2-e]pyrazine
• 英文别名: 7-chloro-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene
• CAS: 240815-50-3
• 化学式: C₉H₅ClN₄
• 分子量: 204.619
• InChiKey: RBCJCRIFWFBXNY-UHFFFAOYSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-6-甲基苯胺 、 6-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到N-(2-Chloro-6-methylphenyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine
  参考文献：
  名称：

  Imidazoquinoxaline Src-Family Kinase p56^Lck Inhibitors:  SAR, QSAR, and the Discovery of (S)-N-(2-Chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl)imidazo- [1,5-a]pyrido[3,2-e]pyrazin-6-amine (BMS-279700) as a Potent and Orally Active Inhibitor with Excellent in Vivo Antiinflammatory Activity

  摘要：

  A series of novel anilino 5-azaimidazoquinoxaline analogues possessing potent in vitro activity against p56(Lck) and T cell proliferation have been discovered. Subsequent SAR studies led to the identification of compound 4 (BMS-279700) as an orally active lead candidate that blocks the production of proinflammatory cytokines (IL-2 and TNFalpha) in vivo. In addition, an expanded set of imidazoquinoxalines provided several descriptive QSAR models highlighting the influence of significant steric and electronic features. The H-bonding (Met319) contribution to observed binding affinities within a tightly congeneric series was found to be significant.

  DOI：

  10.1021/jm030217e
• 作为产物：
  描述：

  N-(2-氯吡啶-3-基)-1H-咪唑-5-羧酰胺 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 18.0h， 生成 6-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪
  参考文献：
  名称：

  Imidazoquinoxaline Src-Family Kinase p56^Lck Inhibitors:  SAR, QSAR, and the Discovery of (S)-N-(2-Chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl)imidazo- [1,5-a]pyrido[3,2-e]pyrazin-6-amine (BMS-279700) as a Potent and Orally Active Inhibitor with Excellent in Vivo Antiinflammatory Activity

  摘要：

  A series of novel anilino 5-azaimidazoquinoxaline analogues possessing potent in vitro activity against p56(Lck) and T cell proliferation have been discovered. Subsequent SAR studies led to the identification of compound 4 (BMS-279700) as an orally active lead candidate that blocks the production of proinflammatory cytokines (IL-2 and TNFalpha) in vivo. In addition, an expanded set of imidazoquinoxalines provided several descriptive QSAR models highlighting the influence of significant steric and electronic features. The H-bonding (Met319) contribution to observed binding affinities within a tightly congeneric series was found to be significant.

  DOI：

  10.1021/jm030217e

文献信息

• HETEROCYCLO-SUBSTITUTED IMIDAZOPYRAZINE PROTEIN TYROSINE KINASE INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1066286B1

  公开（公告）日：2009-04-29
• US5990109A
  申请人：——

  公开号：US5990109A

  公开（公告）日：1999-11-23