ethyl 1-bromoimidazo[1,5-a]pyrazine-3-carboxylate | 1304064-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1,5-a]吡嗪
• 英文名称: ethyl 1-bromoimidazo[1,5-a]pyrazine-3-carboxylate
• 英文别名: Ethyl 1-bromoimidazo[1,5-a]pyrazine-3-carboxylate
• CAS: 1304064-99-0
• 化学式: C₉H₈BrN₃O₂
• 分子量: 270.085
• InChiKey: AHUWOOAHQFAMAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-bromoimidazo[1,5-a]pyrazine-3-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-1-morpholino-N-(2,2,2-trifluoro-1-(pyridin-2-yl)ethyl)imidazo[1,5-a]pyrazine-3-carboxamide
  参考文献：
  名称：

  Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

  摘要：

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.082
• 作为产物：
  描述：

  3-Carbethoxyimidazo<1,5-a>pyrazin 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 ethyl 1-bromoimidazo[1,5-a]pyrazine-3-carboxylate
  参考文献：
  名称：

  [EN] MPRO TARGETING ANTIVIRAL COMPOUNDS
  [FR] COMPOSÉS ANTIVIRAUX CIBLANT LES MPRO

  摘要：

  公开了根据式（I）的新型病毒 Mpro 抑制剂、它们的药学上可接受的盐及其药物组合物。还公开了使用此类化合物和组合物抑制 Mpro 和/或治疗各种病毒感染的方法；特别是与冠状病毒有关的病毒感染。本公开的化合物和组合物在治疗广谱冠状病毒方面可能特别有用。

  公开号：

  WO2023180189A1

文献信息

• [EN] ALKYNYL ALCOHOLS AND METHODS OF USE<br/>[FR] ALCOOLS D'ALCYNYLE ET PROCÉDÉS D'UTILISATION CORRESPONDANTS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015025025A1

  公开（公告）日：2015-02-26

  The invention relates to compounds of Formula (0): wherein Q, A1-A8, R4 and R5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over- activation of NF-kB signaling is observed.

  这项发明涉及以下式的化合物（0）：其中Q，A1-A8，R4和R5分别具有如本文所述的含义。式（0）的化合物及其药物组成物在治疗观察到NF-kB信号通路的不良或过度活化的疾病和紊乱中是有用的。
• ALKYNYL ALCOHOLS AND METHODS OF USE
  申请人：Genentech, Inc.

  公开号：US20150065482A1

  公开（公告）日：2015-03-05

  The invention relates to compounds of Formula (0): wherein Q, A 1 -A 8 , R 4 and R 5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over-activation of NF-kB signaling is observed.

  本发明涉及化合物公式（0）：其中Q，A1-A8，R4和R5的含义如本文所述。公式（0）的化合物及其制药组合物在治疗观察到NF-kB信号不良或过度激活的疾病和疾病中非常有用。
• [EN] MPRO TARGETING ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX CIBLANT LES MPRO
  申请人：EXSCIENTIA AI LTD

  公开号：WO2023180189A1

  公开（公告）日：2023-09-28

  Disclosed are novel viral Mpro inhibitors according to Formula (I), their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. Also disclosed are methods of using such compounds and compositions to inhibit Mpro and/or to treat various viral infections; particularly related to coronavirus. The compounds and compositions of the disclosure may be particularly useful in treating a broad spectrum of coronavirus.

  公开了根据式（I）的新型病毒 Mpro 抑制剂、它们的药学上可接受的盐及其药物组合物。还公开了使用此类化合物和组合物抑制 Mpro 和/或治疗各种病毒感染的方法；特别是与冠状病毒有关的病毒感染。本公开的化合物和组合物在治疗广谱冠状病毒方面可能特别有用。
• US9605005B2
  申请人：——

  公开号：US9605005B2

  公开（公告）日：2017-03-28
• Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy
  作者：B. Wesley Trotter、Kausik K. Nanda、Christopher S. Burgey、Craig M. Potteiger、James Z. Deng、Ahren I. Green、John C. Hartnett、Nathan R. Kett、Zhicai Wu、Darrell A. Henze、Kimberly Della Penna、Reshma Desai、Michael D. Leitl、Wei Lemaire、Rebecca B. White、Suzie Yeh、Mark O. Urban、Stefanie A. Kane、George D. Hartman、Mark T. Bilodeau

  DOI：10.1016/j.bmcl.2011.02.082

  日期：2011.4

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.