7-fluoro-5-iodo-quinolin-8-ol | 38453-32-6

• 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: 7-fluoro-5-iodo-quinolin-8-ol
• 英文别名: 7-fluoro-5-iodo-8-hydroxyquinoline；7-fluoro-5-iodoquinolin-8-ol
• CAS: 38453-32-6
• 化学式: C₉H₅FINO
• 分子量: 289.048
• InChiKey: DEVRWRJFPIOWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-fluoro-5-iodo-quinolin-8-ol 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 caesium carbonate 、 间氯过氧苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 7-fluoro-5-((4-(trifluoromethyl)phenyl)sulfonyl)quinolin-8-ol
  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：

  6-氟-2-氨基苯酚 在 N-碘代丁二酰亚胺 、 硫酸 作用下， 以 氯仿 、 硝基苯 为溶剂， 反应 6.25h， 生成 7-fluoro-5-iodo-quinolin-8-ol
  参考文献：
  名称：

  [EN] COMT INHIBITING METHODS AND COMPOSITIONS
  [FR] PROCÉDÉS D'INHIBITION DE LA COMT ET COMPOSITIONS ASSOCIÉES

  摘要：

  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。

  公开号：

  WO2016123576A1

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。
• [EN] 8-HYDROXYQUINOLINE DERIVATIVES AS DIAGNOSTIC AND THERAPEUTIC AGENTS<br/>[FR] DÉRIVÉS DE 8-HYDROXYQUINOLÉINE EN TANT QU'AGENTS DIAGNOSTIQUES ET THÉRAPEUTIQUES
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2017027064A1

  公开（公告）日：2017-02-16

  The present application provides compounds useful in methods of treating neurological disorders such as Alzheimer's disease, and cancer such as prostate cancer. Also provided herein are radiolabeled compounds useful for imaging techniques, and techniques for diagnosis and monitoring of treatment of neurological disorders and cancer. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography or single- photon emission computed tomography. Methods for preparing radiolabeled compounds and methods for preparing unlabeled compounds are also provided.

  本申请提供了在治疗神经系统疾病如阿尔茨海默病以及癌症如前列腺癌方面有用的化合物。本文还提供了用于成像技术的放射标记化合物，以及用于诊断和监测神经系统疾病和癌症治疗的技术。本文提供的示例放射标记化合物可用作正电子发射断层扫描或单光子发射计算机断层扫描的放射追踪剂。还提供了制备放射标记化合物和非标记化合物的方法。
• COMT Inhibiting Methods and Compositions
  申请人：Lieber Institute for Brain Development

  公开号：US20160222001A1

  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，其对于由COMT介导的各种疾病的治疗具有用处，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：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。
• 8-hydroxyquinoline derivatives as diagnostic and therapeutic agents
  申请人：The General Hospital Corporation

  公开号：US10781178B2

  公开（公告）日：2020-09-22

  The present application provides compounds useful in methods of treating neurological disorders such as Alzheimer's disease, and cancer such as prostate cancer. Also provided herein are radiolabeled compounds useful for imaging techniques, and techniques for diagnosis and monitoring of treatment of neurological disorders and cancer. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography or single-photon emission computed tomography. Methods for preparing radiolabeled compounds and methods for preparing unlabeled compounds are also provided.

  本申请提供了用于治疗神经系统疾病（如阿尔茨海默病）和癌症（如前列腺癌）的化合物。本申请还提供了用于成像技术的放射性标记化合物，以及用于诊断和监测神经系统疾病和癌症治疗的技术。本文提供的一种示例性放射性标记化合物可用作正电子发射计算机断层扫描或单光子发射计算机断层扫描的放射性示踪剂。还提供了制备放射性标记化合物的方法和制备未标记化合物的方法。