7-Fluoro-4-hydroxy-1H-quinolin-2-one | 71886-20-9

• 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-4-hydroxy-1H-quinolin-2-one
• 英文别名: 7-fluoro-4-hydroxyquinolin-2(1H)-one
• CAS: 71886-20-9
• 化学式: C₉H₆FNO₂
• 分子量: 179.151
• InChiKey: JYJYIFHHYIEUCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Fluoro-4-hydroxy-1H-quinolin-2-one 在 四磷十氧化物 、 四丁基溴化铵 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 生成 4-bromo-7-fluoroquinolin-2(1H)-one
  参考文献：
  名称：

  Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells

  摘要：

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.012
• 作为产物：
  描述：

  3-氟苯胺 、 丙二酸 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以89%的产率得到7-Fluoro-4-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones

  摘要：

  3-Unsubstituted 4-hydroxyquinolin-2(1H)-one containing F and CF3 substituent in ring is important pharmacological and synthetic target and basic synthones for a number of antibacterial fluoroquinolones and is promising potent and selective glycine site NMDA receptors. A simple facile one-step microwave enhanced multigram synthesis of such fluorinated quinolones in reasonable purity has been developed in excellent yield (85-94%) in 3-5min, whereas conventional synthesis required the harsh conditions, long reaction period with use of environmentally unacceptable regents giving the required product in lower yield, The phototoxicity as well as the cytotoxic activities of the title compounds are evaluated against leukemia- and adenocarcinoma-derived cell lines in comparison to the normal human keratinocytes. Structure-activity relationships between the chemical structures and the antimycobacterial, antifungal activity of the evaluated compounds are also discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.082

文献信息

• 一种二元电解质及其制备和应用
  申请人：北京卫蓝新能源科技有限公司

  公开号：CN114230588A

  公开（公告）日：2022-03-25

  本发明涉及一种二元电解质及其制备和应用，所述二元电解质包括以下通式I所表示的三氟化硼盐：在通式Ⅰ中，R1、R2、R3可独立地为无、链或环；且R1、R2、R3不同时为无；R1、R2或R3中含有一个‑OBF3M；当R1、R2或R3中含有环时，该环为均由C原子构成的环或含有至少一个杂原子的环；当R1、R2或R3为链时，其为仅由C原子构成的链或含有非碳原子的链，该链为饱和链或含有不饱和键的链，所述不饱和键包括双键和/或三键；R1、R2或R3上连接第一取代基。本申请中的电解质创造性的将两个‑OBF3M复合于一个化合物中，其可作为电解质盐又可作为添加剂，效果佳。
• An efficient synthesis of fluorine-containing substituted spiro[piperidine-4,4′-pyrano[3,2-c]quinoline]-3′-carbonitrile by nonconventional methods
  作者：Anshu Dandia、Sangeeta Gautam、Anuj Kumar Jain

  DOI：10.1016/j.jfluchem.2007.08.002

  日期：2007.12

  A series of fluorine-containing substituted spiro[piperidine-4,4'-pyrano[3,2-c]quinolines] were synthesized through a rapid one-pot multicomponent reaction under microwave irradiation and sonication. The method has the advantages of excellent yields (80-96%) and short reaction time (3-10 min). We provide a series of fluorinated quinoline derivatives interesting for biological screening tests. (C) 2007 Published by Elsevier B.V.
• Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells
  作者：Clemens Zwergel、Brigitte Czepukojc、Emilie Evain-Bana、Zhanjie Xu、Giulia Stazi、Mattia Mori、Alexandros Patsilinakos、Antonello Mai、Bruno Botta、Rino Ragno、Denise Bagrel、Gilbert Kirsch、Peter Meiser、Claus Jacob、Mathias Montenarh、Sergio Valente

  DOI：10.1016/j.ejmech.2017.04.012

  日期：2017.7

  Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhibitors on the one hand la-k, coumarin-based, and on the other 2a-g, quinolinone-based, which inhibit either enzymes up to a sub-micro molar level and at single digit micro molar concentrations, respectively. When tested in six different cancer cell lines, compound 2c displayed the highest efficacy to arrest cell viability, showing in almost all cell lines sub-micro molar IC50 values, a profile even better than the reference compound NCS95397. To investigate the putative binding mode of the inhibitors and to develop quantitative structure-activity relationships, molecular docking and 3-D QSAR studies were also carried out. Four selected inhibitors, la, ld, 2a and 2c have been also tested in A431 cancer cells; among them, compound 2c was the most potent one leading to cell proliferation arrest and decreased CDC25C protein levels together with its splicing variant. Compound 2c displayed increased phosphorylation levels of histone H3, induction of PARP and caspase 3 cleavage, highlighting its contribution to cell death through pro-apoptotic effects. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones
  作者：Kapil Arya、Manish Agarwal

  DOI：10.1016/j.bmcl.2006.09.082

  日期：2007.1

  3-Unsubstituted 4-hydroxyquinolin-2(1H)-one containing F and CF3 substituent in ring is important pharmacological and synthetic target and basic synthones for a number of antibacterial fluoroquinolones and is promising potent and selective glycine site NMDA receptors. A simple facile one-step microwave enhanced multigram synthesis of such fluorinated quinolones in reasonable purity has been developed in excellent yield (85-94%) in 3-5min, whereas conventional synthesis required the harsh conditions, long reaction period with use of environmentally unacceptable regents giving the required product in lower yield, The phototoxicity as well as the cytotoxic activities of the title compounds are evaluated against leukemia- and adenocarcinoma-derived cell lines in comparison to the normal human keratinocytes. Structure-activity relationships between the chemical structures and the antimycobacterial, antifungal activity of the evaluated compounds are also discussed. (c) 2006 Elsevier Ltd. All rights reserved.