ethyl 8-fluoro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate | 1159706-44-1

• 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: ethyl 8-fluoro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate
• 英文别名: ethyl 8-fluoro-3-hydroxy-2-oxo-1H-quinoline-4-carboxylate
• CAS: 1159706-44-1
• 化学式: C₁₂H₁₀FNO₄
• 分子量: 251.214
• InChiKey: ZLWHKMCFNASYTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 8-fluoro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以81%的产率得到8-fluoro-3-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  手性氢键合铱敏化剂控制的对映选择性激发态光反应

  摘要：

  电子激发态的立体化学控制是光化学合成中的长期挑战，很少有人知道在三重态光反应中产生高对映选择性的催化体系。我们在这里报告了一种异常有效的手性光催化剂，它使用一系列氢键和π-π相互作用募集前手性喹诺酮。这些底物在过渡金属光敏剂的手性环境中的组织导致有效的德克斯特能量转移和有效的立体感应。这些有机金属发色团对配体修饰的相对不敏感性使得该催化剂结构的优化对于在催化剂负载量下高对映体过量的情况比报道的类似手性有机光敏剂的最佳条件低了100倍。

  DOI：

  10.1021/jacs.7b10586
• 作为产物：
  描述：

  7-氟吲哚满二酮 在 盐酸 、 二乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 74.0h， 生成 ethyl 8-fluoro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate
  参考文献：
  名称：

  Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity

  摘要：

  We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selective inhibitory properties in the 10-20 mu M range against HIV-1 reverse transcriptase associated ribonuclease H activity, without affecting the integrase and reverse transcriptase DNA polymerase activities. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.096

文献信息

• [EN] QUINOLINONE CARBOXAMIDE INHIBITORS OF ENDOTHELIAL LIPASE<br/>[FR] INHIBITEURS QUINOLÉINONE CARBOXAMIDE DE LIPASE ENDOTHÉLIALE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013048942A1

  公开（公告）日：2013-04-04

  The present invention provides compounds of Formula (I): as defined in the specification and compositions comprising any of such novel compounds. These compounds are endothelial lipase inhibitors which may be used as medicaments.

  本发明提供了如规范中定义的Formula (I)的化合物，以及包含任何此类新化合物的组合物。这些化合物是内皮脂酶抑制剂，可用作药物。
• Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer
  作者：Kazimer L. Skubi、Jesse B. Kidd、Hoimin Jung、Ilia A. Guzei、Mu-Hyun Baik、Tehshik P. Yoon

  DOI：10.1021/jacs.7b10586

  日期：2017.11.29

  transition-metal photosensitizer leads to efficient Dexter energy transfer and effective stereoinduction. The relative insensitivity of these organometallic chromophores toward ligand modification enables the optimization of this catalyst structure for high enantiomeric excess at catalyst loadings as much as 100-fold lower than the optimal conditions reported for analogous chiral organic photosensitizers.

  电子激发态的立体化学控制是光化学合成中的长期挑战，很少有人知道在三重态光反应中产生高对映选择性的催化体系。我们在这里报告了一种异常有效的手性光催化剂，它使用一系列氢键和π-π相互作用募集前手性喹诺酮。这些底物在过渡金属光敏剂的手性环境中的组织导致有效的德克斯特能量转移和有效的立体感应。这些有机金属发色团对配体修饰的相对不敏感性使得该催化剂结构的优化对于在催化剂负载量下高对映体过量的情况比报道的类似手性有机光敏剂的最佳条件低了100倍。
• [EN] HYDROXYQUINOLIN-2(1H)-ONES AND DERIVATIVES THEREOF<br/>[FR] HYDROXYQUINOLIN-2(1H)-ONES ET LEURS DÉRIVÉS
  申请人：PFIZER

  公开号：WO2010058314A1

  公开（公告）日：2010-05-27

  This invention relates to known and novel hydroxyquinolin-2(1H)-ones and derivatives thereof which are useful for the treatment of cognitive-related disorders and neuropathic pain disorders in a mammal, e.g., a human. The invention also relates to pharmaceutical compositions containing such compounds.

  这项发明涉及已知和新型的羟基喹啉-2(1H)-酮及其衍生物，可用于治疗哺乳动物（例如人类）的认知相关障碍和神经病性疼痛障碍。该发明还涉及含有这类化合物的药物组合物。
• QUINOLINONE CARBOXAMIDE INHIBITORS OF ENDOTHELIAL LIPASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20140243314A1

  公开（公告）日：2014-08-28

  The present invention provides compounds of Formula (I): as defined in the specification and compositions comprising any of such novel compounds. These compounds are endothelial lipase inhibitors which may be used as medicaments.

  本发明提供了以下式子（I）的化合物：如规范所定义的和包含任何此类新化合物的组合物。这些化合物是内皮细胞脂肪酶抑制剂，可用作药物。
• Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1<i>H</i>)-one Series of Potent <scp>d</scp>-Amino Acid Oxidase (DAAO) Inhibitors
  作者：Allen J. Duplantier、Stacey L. Becker、Michael J. Bohanon、Kris A. Borzilleri、Boris A. Chrunyk、James T. Downs、Lain-Yen Hu、Ayman El-Kattan、Larry C. James、Shenping Liu、Jiemin Lu、Noha Maklad、Mahmoud N. Mansour、Scot Mente、Mary A. Piotrowski、Subas M. Sakya、Susan Sheehan、Stefanus J. Steyn、Christine A. Strick、Victoria A. Williams、Lei Zhang

  DOI：10.1021/jm900128w

  日期：2009.6.11

  3-Hydroxyquinolin-2(1H)-one (2) was discovered by high throughput screening in a functional assay to be a potent inhibitor of human DAAO, and its binding affinity was confirmed in a Biacore assay. Cocrystallization of 2 with the human DAAO enzyme defined the binding site and guided the design of new analogues. The SAR, pharmacokinetics, brain exposure, and effects on cerebellum D-serine are described. Subsequent evaluation against the rat DAAO enzyme revealed a divergent SAR versus the human enzyme and may explain the high exposures of drug necessary to achieve significant changes in rat or mouse cerebellum D-serine.