4-羟基-5-甲氧基喹啉-3-甲腈 | 331662-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-羟基-5-甲氧基喹啉-3-甲腈
• 英文名称: 4-hydroxy-5-methoxy-3-quinolinecarbonitrile
• 英文别名: 5-methoxy-4-oxo-1H-quinoline-3-carbonitrile
• CAS: 331662-64-7
• 化学式: C₁₁H₈N₂O₂
• 分子量: 200.197
• InChiKey: FBZWGJLDVKSZDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4-羟基-5-甲氧基喹啉-3-甲腈 在 三氯氧磷 作用下， 生成 4-氯-5-甲氧基-3-喹啉甲腈
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of 3-Cyano-4-(phenoxyanilino)quinolines as MEK (MAPKK) Inhibitors

  摘要：

  A series of 3-cyano-4-(phenoxyanilino)cyanoquinolines has been prepared as MEK (MAP kinase kinase) inhibitors. The best activity is seen with alkoxy groups at both the 6- and 7-positions. The lead compounds show low nanomolar IC50's against MAP kinase kinase, and have potent inhibitory activity in tumor cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00580-1
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯甲酸甲酯 以 四氢呋喃 为溶剂， 生成 4-羟基-5-甲氧基喹啉-3-甲腈
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of 3-Cyano-4-(phenoxyanilino)quinolines as MEK (MAPKK) Inhibitors

  摘要：

  A series of 3-cyano-4-(phenoxyanilino)cyanoquinolines has been prepared as MEK (MAP kinase kinase) inhibitors. The best activity is seen with alkoxy groups at both the 6- and 7-positions. The lead compounds show low nanomolar IC50's against MAP kinase kinase, and have potent inhibitory activity in tumor cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00580-1

文献信息

• Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor
  作者：Jennifer Tsoung、Andrew R. Bogdan、Stanislaw Kantor、Ying Wang、Manwika Charaschanya、Stevan W. Djuric

  DOI：10.1021/acs.joc.6b02520

  日期：2017.1.20

  pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents

  在自动化的Phoenix高温高压连续流反应器中，数分钟之内即可合成出对药物研究潜在感兴趣的熔融嘧啶酮和喹诺酮衍生物，收率高达96％。难于合成或需要多步操作的杂环支架可使用一组常见的反应条件轻松获得。低沸点溶剂的使用以及这些反应的高转化率使得易于后处理和分离。本文报道的方法高度适合于快速和有效的杂环合成以及化合物的放大。
• HETEROCYCLIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS, IN PARTICULAR AS ANTI-ALZHEIMER AGENTS
  申请人：Marsais Francis

  公开号：US20090062279A1

  公开（公告）日：2009-03-05

  The invention is related to compound which comprises at least one radical C═Y, Y being O or S, and an oxidable and non protonable nitrogen atom N wherein the distance (d) between the at least one carbon atom of the radical group C═Y and the nitrogen atom, when oxidized, is comprised between 0.3 and 0.8 nanometers. The invention is related to new heterocyclic compounds defined by formula G, their preparation, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly in the treatment of neurodegenerative or Alzheimer disease.

  本发明涉及一种化合物，其包含至少一个基团C═Y，其中Y为O或S，以及一个可氧化且不可质子化的氮原子N，其中在氧化时，基团C═Y的至少一个碳原子与氮原子之间的距离(d)在0.3至0.8纳米之间。本发明涉及由公式G定义的新杂环化合物及其制备方法，涉及包含它们的制药组合物以及它们在治疗神经退行性或阿尔茨海默病方面的用途。
• Synthesis and Src Kinase Inhibitory Activity of a Series of 4-Phenylamino-3-quinolinecarbonitriles
  作者：Diane H. Boschelli、Yanong D. Wang、Fei Ye、Biqi Wu、Nan Zhang、Minu Dutia、Dennis W. Powell、Allan Wissner、Kim Arndt、Jennifer M. Weber、Frank Boschelli

  DOI：10.1021/jm000420z

  日期：2001.3.1

  Screening of a directed compound library in a yeast-based assay identified 4-[(2,4-dichlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile (2a) as a Src inhibitor. An enzymatic assay established that 2a was an ATP-competitive inhibitor of the kinase activity of Src. We present here SAR data for 2a which shows that the aniline group at C-4, the carbonitrile group at C-3, and the alkoxy groups at C-6 and C-7 of the quinoline are crucial for optimal activity. Increasing the size of the C-2 substituent of the aniline at C-4 of 2a from chloro to bromo to iodo resulted in a corresponding increase in Src inhibition. Furthermore, replacement of the 7-methoxy group of 2a with various 3-heteroalkylaminopropoxy groups provided increased inhibition of both Src enzymatic and cellular activity. Compound 25, which contains a 3-morpholinopropoxy group, had an IC50 of 3.8 nM in the Src enzymatic assay and an IC50 of 940 nM for the inhibition of Src-dependent cell proliferation.
• NEW HETEROCYCLIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS, IN PARTICULAR AS ANTI-ALZHEIMER AGENTS
  申请人：VFP Therapies

  公开号：EP1868998B1

  公开（公告）日：2016-05-25
• US7977354B2
  申请人：——

  公开号：US7977354B2

  公开（公告）日：2011-07-12