6-(2-furyl)[5H]pyrrolo[2,3-b]pyrazine

• 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: 6-(2-furyl)[5H]pyrrolo[2,3-b]pyrazine
• 英文别名: 6-(furan-2-yl)-5H-pyrrolo[2,3-b]pyrazine
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: PGQDMRRDTMOOLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基吡嗪 、 2-氰基呋喃 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 生成 6-(2-furyl)[5H]pyrrolo[2,3-b]pyrazine
  参考文献：
  名称：

  Pyrrolopyrazines as kinase inhibitors

  摘要：

  该发明涉及具有一般式(I)的吡咯并[2,3b]-吡嗪衍生物：   其中：R2和R3相同或不同，代表H，C1-C6烷基，所述烷基为直链或支链烷基，可以被取代，R6是可选择被取代的芳香环Ar或环烷基，所述环烷基可被芳基取代，R7是H，C1-C6烷基，(烷基)n-卤，CH2-CH = CH2，CH2-环烷基，CH2-Ar，其中"烷基"是C1-C6烷基，n为1-6，Z为H或CH3。用作药物组合物的活性成分，特别用于治疗或预防神经退行性疾病和增殖性疾病。

  公开号：

  EP1388541A1

文献信息

• Aloisines, a New Family of CDK/GSK-3 Inhibitors. SAR Study, Crystal Structure in Complex with CDK2, Enzyme Selectivity, and Cellular Effects
  作者：Yvette Mettey、Marie Gompel、Virginie Thomas、Matthieu Garnier、Maryse Leost、Irène Ceballos-Picot、Martin Noble、Jane Endicott、Jean-michel Vierfond、Laurent Meijer

  DOI：10.1021/jm020319p

  日期：2003.1.1

  Cyclin-dependent kinases (CDKs) regulate the cell cycle, apoptosis, neuronal functions, transcription, and exocytosis. The observation of CDK deregulations in various pathological situations suggests that CDK inhibitors may have a therapeutic value. In this article, we report on the identification of 6-phenyl[5H]pyrrolo[2,3-b]pyrazines (aloisines) as a novel potent CDK inhibitory scaffold. A selectivity study performed on 26 kinases shows that aloisine A is highly selective for CDK1/cyclin B, CDK2/cyclin A-E, CDK5/p25, and GSK-3alpha/beta; the two latter enzymes have been implicated in Alzheimer's disease. Kinetic studies, as well as the resolution of a CDK2-aloisine cocrystal structure, demonstrate that aloisines act by competitive inhibition of ATP binding to the catalytic subunit of the kinase. As observed with all inhibitors reported so far, aloisine interacts with the ATP-binding pocket through two hydrogen bonds with backbone nitrogen and oxygen atoms of Leu 83. Aloisine inhibits cell proliferation by arresting cells in both G1 and G2.
• Derivatives of Pyrrolo-Pyrazines Having a Kinase Inhibitory Activity and Their Biological Applications
  申请人：Meijer Laurent

  公开号：US20080161312A1

  公开（公告）日：2008-07-03

  The invention relates to pyrrolo[2,3b]-pyrazine derivatives having the general Formula (I) wherein R2 and R3 are identical or different and represent H, C1-C6 alkyl, said alkyl being a straight or branched-chain alkyl, which can be substituted, R6 is an optionally substituted aromatic cycle Ar or a cycloalkyl, said cycloalkyl being optionally substituted by an aryl group which can also be substituted, R7 is H, C1-C6 alkyl, (alk.)n-hal., CH2—CH═CH2, CH2-cycloalkyl, CH2—Ar, with “alk.” being a C1-C6 alkylene group, n being 1-6, Z is H or CH3. Application as active principle of pharmaceutical compositions, particularly for treating or preventing neurodegenerative disorders and proliferative disorders.
• US8106050B2
  申请人：——

  公开号：US8106050B2

  公开（公告）日：2012-01-31
• Pyrrolopyrazines as kinase inhibitors
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1388541A1

  公开（公告）日：2004-02-11

  The invention relates to pyrrolo [2,3b]-pyrazine derivatives having the general formula (I) :    wherein : R2 and R3 are identical or different and represent H, C1-C6 alkyl, said alkyl being a straight or branched-chain alkyl, which can be substituted, R6 is an optionally substituted aromatic cycle Ar or a cycloalkyl, said cycloalkyl being optionally substituted by an aryl group which can also be substituted, R7 is H, C1-C6 alkyl, (alk.)n-hal., CH2-CH = CH2, CH2-cycloalkyl, CH2-Ar, with "alk." being a C1-C6 alkylene group, n being 1-6, Z is H or CH3. Application as active principle of pharmaceutical compositions, particularly for treating or preventing neurodegenerative disorders and proliferative disorders.

  该发明涉及具有一般式(I)的吡咯并[2,3b]-吡嗪衍生物：   其中：R2和R3相同或不同，代表H，C1-C6烷基，所述烷基为直链或支链烷基，可以被取代，R6是可选择被取代的芳香环Ar或环烷基，所述环烷基可被芳基取代，R7是H，C1-C6烷基，(烷基)n-卤，CH2-CH = CH2，CH2-环烷基，CH2-Ar，其中"烷基"是C1-C6烷基，n为1-6，Z为H或CH3。用作药物组合物的活性成分，特别用于治疗或预防神经退行性疾病和增殖性疾病。