(R)-4-[6-[(2-Chloro-6-methylphenyl)amino]imidazo[1,5-a]pyrido[3,2-e]pyrazin-2-yl]-2-piperazinemethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-4-[6-[(2-Chloro-6-methylphenyl)amino]imidazo[1,5-a]pyrido[3,2-e]pyrazin-2-yl]-2-piperazinemethanol
• 英文别名: [(2R)-4-[7-(2-chloro-6-methylanilino)-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-12-yl]piperazin-2-yl]methanol
• 化学式: C₂₁H₂₂ClN₇O
• 分子量: 423.905
• InChiKey: OOCDCJVAHKFZHI-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6-二氯-3-氨基吡啶 在 sodium hexamethyldisilazane 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 生成 (R)-4-[6-[(2-Chloro-6-methylphenyl)amino]imidazo[1,5-a]pyrido[3,2-e]pyrazin-2-yl]-2-piperazinemethanol
  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
• RENIN INHIBITORS
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：EP2010488A2

  公开（公告）日：2009-01-07
• US5990109A
  申请人：——

  公开号：US5990109A

  公开（公告）日：1999-11-23
• [EN] RENIN INHIBITORS<br/>[FR] INHIBITEURS DE LA RÉNINE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2007117559A2

  公开（公告）日：2007-10-18

  (EN) Described are compounds of the formula ( I ) which are orally active and bind to aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also described are methods of use of the compounds described herein in ameliorating or treating aspartic protease related disorders in a subject in need thereof.(FR) L'invention concerne des composés actifs oralement et qui se lient à des protéases aspartiques, de manière à inhiber leur activité. Lesdits composés sont utilisés dans le traitement ou l'amélioration de maladies associées à l'activités des protéases aspartiques. L'invention concerne également des procédés d'utilisation des composés spécifiés dans la description, permettant l'amélioration ou le traitement de troubles liés aux protéases aspartiques chez un sujet nécessitant ces soins.