8-fluoro-7-methylquinoline | 1420794-63-3

• 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
• 英文名称: 8-fluoro-7-methylquinoline
• 英文别名: 8-Fluoro-7-methylquinoline
• CAS: 1420794-63-3
• 化学式: C₁₀H₈FN
• 分子量: 161.179
• InChiKey: HVEWBBAQMKACPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-fluoro-7-methylquinoline 在 氯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 31.25h， 生成 8-tert-butoxy-7-methyl-5-pyrrolidin-1-ylsulfonylquinoline
  参考文献：
  名称：

  Optimization of 8-Hydroxyquinolines as Inhibitors of Catechol O-Methyltransferase

  摘要：

  A series of 8-hydroxy quinolines were identified as potent inhibitors of catechol O-methyltransferase (COMT) with selectivity for the membrane-bound form of the enzyme. Small substituents at the 7-position of the quinoline were found to increase metabolic stability without sacrificing potency. Compounds with good pharmacokinetics and brain penetration were identified and demonstrated in vivo modulation of dopamine metabolites in the brain. An X-ray cocrystal structure of compound 21 in the S-COMT active site shows chelation of the active site magnesium similar to catechol-based inhibitors. These compounds should prove useful for treatment of many neurological and psychiatric conditions associated with compromised cortical dopamine signaling.

  DOI：

  10.1021/acs.jmedchem.8b01126
• 作为产物：
  描述：

  2-氟-3-甲基苯胺 、 甘油 在 硫酸 、 sodium 3-nitrobenzenesulfonate 作用下， 以88%的产率得到8-fluoro-7-methylquinoline
  参考文献：
  名称：

  Optimization of 8-Hydroxyquinolines as Inhibitors of Catechol O-Methyltransferase

  摘要：

  A series of 8-hydroxy quinolines were identified as potent inhibitors of catechol O-methyltransferase (COMT) with selectivity for the membrane-bound form of the enzyme. Small substituents at the 7-position of the quinoline were found to increase metabolic stability without sacrificing potency. Compounds with good pharmacokinetics and brain penetration were identified and demonstrated in vivo modulation of dopamine metabolites in the brain. An X-ray cocrystal structure of compound 21 in the S-COMT active site shows chelation of the active site magnesium similar to catechol-based inhibitors. These compounds should prove useful for treatment of many neurological and psychiatric conditions associated with compromised cortical dopamine signaling.

  DOI：

  10.1021/acs.jmedchem.8b01126

文献信息

• [EN] COMT INHIBITING METHODS AND COMPOSITIONS<br/>[FR] PROCÉDÉS D'INHIBITION DE LA COMT ET COMPOSITIONS ASSOCIÉES
  申请人：LIEBER INST FOR BRAIN DEV

  公开号：WO2016123576A1

  公开（公告）日：2016-08-04

  The present inventions include a method of inhibiting COMT enzyme in a subject as well as compounds of formula I, or a pharmaceutically acceptable salt thereof, that are useful in the treatment of various disorders mediated by COMT, including Parkinson's disease and/or schizophrenia.

  这些发明包括一种抑制受试者中COMT酶的方法，以及式I的化合物或其药用可接受盐，这些化合物在治疗由COMT介导的各种疾病中有用，包括帕金森病和/或精神分裂症。
• COMT Inhibiting Methods and Compositions
  申请人：Lieber Institute for Brain Development

  公开号：US20160222011A1

  公开（公告）日：2016-08-04

  The present inventions include a method of inhibiting COMT enzyme in a subject as well as compounds of formula I, or a pharmaceutically acceptable salt thereof, that are useful in the treatment of various disorders mediated by COMT, including Parkinson's disease and/or schizophrenia.

  本发明涉及一种抑制受试者中COMT酶的方法，以及公式I的化合物或其药学上可接受的盐，用于治疗由COMT介导的各种疾病，包括帕金森病和/或精神分裂症。
• NOVEL BIPHENYL COMPOUND OR SALT THEREOF
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：EP3632897A1

  公开（公告）日：2020-04-08

  The present invention provides a compound represented by Formula (I) or a salt thereof; an LSD1 inhibitor that contains the compound or a salt thereof as an active ingredient; a pharmaceutical composition that contains the compound or a salt thereof; and an antitumor agent that contains the compound or a salt thereof as an active ingredient.

  本发明提供了一种由式（I）代表的化合物或其盐类；一种含有该化合物或其盐类作为活性成分的 LSD1 抑制剂；一种含有该化合物或其盐类的药物组合物；以及一种含有该化合物或其盐类作为活性成分的抗肿瘤剂。
• COMT inhibiting methods and compositions
  申请人：Lieber Institute for Brain Development

  公开号：US10035799B2

  公开（公告）日：2018-07-31

  The present inventions include a method of inhibiting COMT enzyme in a subject as well as compounds of formula I, or a pharmaceutically acceptable salt thereof, that are useful in the treatment of various disorders mediated by COMT, including Parkinson's disease and/or schizophrenia.

  本发明包括一种抑制受试者体内 COMT 酶的方法，以及可用于治疗由 COMT 介导的各种疾病（包括帕金森病和/或精神分裂症）的式 I 化合物或其药学上可接受的盐。
• Biphenyl compound or salt thereof
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：US10723742B2

  公开（公告）日：2020-07-28

  A compound or a salt thereof represented by Formula (I). An LSD1 inhibitor containing the compound or a salt thereof as an active ingredient. A pharmaceutical composition containing the compound or salt thereof. An antitumor agent containing the compound or a salt thereof as an active ingredient.

  由式（I）代表的化合物或其盐。以该化合物或其盐为活性成分的 LSD1 抑制剂。含有该化合物或其盐的药物组合物。一种含有该化合物或其盐作为活性成分的抗肿瘤剂。