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：——
• Imidazoquinoxaline Src-Family Kinase p56^Lck Inhibitors:  SAR, QSAR, and the Discovery of (<i>S</i>)-<i>N</i>-(2-Chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl)imidazo- [1,5-<i>a</i>]pyrido[3,2-<i>e</i>]pyrazin-6-amine (BMS-279700) as a Potent and Orally Active Inhibitor with Excellent in Vivo Antiinflammatory Activity
  作者：Ping Chen、Arthur M. Doweyko、Derek Norris、Henry H. Gu、Steven H. Spergel、Jagabundhu Das、Robert V. Moquin、James Lin、John Wityak、Edwin J. Iwanowicz、Kim W. McIntyre、David J. Shuster、Kamelia Behnia、Saeho Chong、Henry de Fex、Suhong Pang、Sydney Pitt、Ding Ren Shen、Sara Thrall、Paul Stanley、Octavian R. Kocy、Mark R. Witmer、Steven B. Kanner、Gary L. Schieven、Joel C. Barrish

  DOI：10.1021/jm030217e

  日期：2004.8.1

  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.