7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine | 1422772-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine
• 英文别名: 7-iodo-2-(3,4,5-trimethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine
• CAS: 1422772-46-0
• 化学式: C₁₅H₁₄IN₃O₃
• 分子量: 411.199
• InChiKey: KNSVIOUBBBCAPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine 在 palladium diacetate 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 18.5h， 生成 5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide
  参考文献：
  名称：

  Pyrrolopyrazines as Selective Spleen Tyrosine Kinase Inhibitors

  摘要：

  We describe the discovery of several pyrrolopyrazines as potent and selective Syk inhibitors and the efforts that eventually led to the desired improvements in physicochemical properties and human whole blood potencies. Ultimately, our mouse model revealed unexpected toxicity that precluded us from further advancing this series.

  DOI：

  10.1021/jm301720p
• 作为产物：
  描述：

  5-溴-4,7-二氮杂吲哚 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine
  参考文献：
  名称：

  Pyrrolopyrazines as Selective Spleen Tyrosine Kinase Inhibitors

  摘要：

  We describe the discovery of several pyrrolopyrazines as potent and selective Syk inhibitors and the efforts that eventually led to the desired improvements in physicochemical properties and human whole blood potencies. Ultimately, our mouse model revealed unexpected toxicity that precluded us from further advancing this series.

  DOI：

  10.1021/jm301720p

文献信息

• Pyrrolopyrazine kinase inhibitors
  申请人：Roche Palo Alto

  公开号：US08008298B2

  公开（公告）日：2011-08-30

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables Q1, R, and X are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及一种新型吡咯吡嗪衍生物的使用，其化学式为I，其中变量Q1、R和X的定义如本文所述，该衍生物抑制JAK和SYK，有助于治疗自身免疫和炎症性疾病。
• PYRROLOPYRAZINE KINASE INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2245033A1

  公开（公告）日：2010-11-03
• US8008298B2
  申请人：——

  公开号：US8008298B2

  公开（公告）日：2011-08-30
• [EN] PYRROLOPYRAZINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRROLOPYRAZINE KINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009106441A1

  公开（公告）日：2009-09-03

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables Q1, R, and X are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.
• Pyrrolopyrazines as Selective Spleen Tyrosine Kinase Inhibitors
  作者：Fernando Padilla、Niala Bhagirath、Shaoqing Chen、Eric Chiao、David M. Goldstein、Johannes C. Hermann、Jonathan Hsu、Joshua J. Kennedy-Smith、Andreas Kuglstatter、Cheng Liao、Wenjian Liu、Lee E. Lowrie、Kin Chun Luk、Stephen M. Lynch、John Menke、Linghao Niu、Timothy D. Owens、Counde O-Yang、Aruna Railkar、Ryan C. Schoenfeld、Michelle Slade、Sandra Steiner、Yun-Chou Tan、Armando G. Villaseñor、Ce Wang、Jutta Wanner、Wenwei Xie、Daigen Xu、Xiaohu Zhang、Mingyan Zhou、Matthew C. Lucas

  DOI：10.1021/jm301720p

  日期：2013.2.28

  We describe the discovery of several pyrrolopyrazines as potent and selective Syk inhibitors and the efforts that eventually led to the desired improvements in physicochemical properties and human whole blood potencies. Ultimately, our mouse model revealed unexpected toxicity that precluded us from further advancing this series.