2-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪-6-醇 | 240815-52-5

• 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: 2-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪-6-醇
• 英文名称: 2-chloroimidazo[1,5-a]pyrido[3,2-e]pyrazin-6(5H)-one
• 英文别名: 12-chloro-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-7-one
• CAS: 240815-52-5
• 化学式: C₉H₅ClN₄O
• 分子量: 220.618
• InChiKey: XOVDCRJSULXUPB-UHFFFAOYSA-N

物化性质

• 沸点：
  355.6±42.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪-6-醇 在 sodium hexamethyldisilazane 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-(2-chloro-6-methylphenyl)-2-(1-piperazinyl)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：

  2,6-二氯-3-氨基吡啶 在 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 生成 2-氯咪唑并[1,5-a]吡啶并[3,2-e]吡嗪-6-醇
  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

• Synthesis of imidazo[1,5-a]quinoxalin-4(5H)-one template via a novel intramolecular cyclization process
  作者：Derek Norris、Ping Chen、Joel C Barrish、Jagabandhu Das、Robert Moquin、Bang-Chi Chen、Peng Guo

  DOI：10.1016/s0040-4039(01)00698-0

  日期：2001.6

  A novel, efficient, and regiospecific method for the construction of the imidazo[1,5-a]quinoxalin-4(5H)-one template is described. The key reaction involves an intramolecular cyclization process and provides the desired products in excellent yield.

  描述了一种新颖，有效且针对区域的方法，用于构建咪唑并[1,5 - a ]喹喔啉-4（5 H）-one模板。关键反应涉及分子内环化过程，并以优异的产率提供所需的产物。
• 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
• KR20220146002A
  申请人：——

  公开号：——

  公开（公告）日：——