ethyl 1-ethyl-7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate | 53977-11-0

• 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 1-ethyl-7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• 英文别名: Ethyl 1-ethyl-7-fluoro-4-quinolone-3-carboxylate；ethyl 1-ethyl-7-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 53977-11-0
• 化学式: C₁₄H₁₄FNO₃
• 分子量: 263.268
• InChiKey: FRSYIBLQNGWKES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 ethyl 1-ethyl-7-fluoro-4-(propylimino)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Van Es, Theodorus; Staskun, Benjamin, South African Journal of Chemistry, 2001, vol. 54, p. 102 - 117

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氟苯胺 在 diphenyl ether-biphenyl eutectic 、 potassium carbonate 作用下， 反应 3.0h， 生成 ethyl 1-ethyl-7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  An NMR Study of Halogenated 1,4-Dihydro-1-ethyl-4-oxoquinoline-3-carboxylates

  摘要：

  Ethyl 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylate and 29 of its mono-, di- and tri-fluoro and/or -chloro derivatives were synthesized and their H-1, C-13 and F-19 NMR spectra were recorded. H-1,C-13 and F-19 chemical shifts, J(HH), J(FH), J(CF) and J(FF) coupling constants are reported. The C-13 substituent chemical shift values of the chloro and fluoro substituents were calculated by linear multiple regression.

  DOI：

  10.1002/(sici)1097-458x(199611)34:11<972::aid-omr994>3.0.co;2-9

文献信息

• 一种含嘧啶环的喹诺酮类衍生物及其制备方法 和用途
  申请人：复旦大学

  公开号：CN103965163B

  公开（公告）日：2016-01-20

  本发明属于医药技术领域,具体为一种含嘧啶环的喹诺酮类衍生物及其制备方法和用途。本发明的化合物为含嘧啶环的喹诺酮类衍生物，还包括其药用盐，水合物和溶剂化物，其多晶或共晶，其同样生物功能的前体和衍生物。本发明还包括其制备方法，以及含有一个或多个此类化合物的组合物在治疗艾滋病等相关药物中的应用。药理实验结果表明，该类化合物具有显著的抗HIV-1病毒活性，可以有效地抑制HIV-1感染的MT-4细胞的复制，而且具有较低的细胞毒性。
• Regioselective Nucleophilic Substitution of Halogen Derivatives of 1-Substituted 4-Oxo-1,4-dihydroquinoline-3-carboxylic Acids
  作者：István Hermecz、Lelle Vasvári-Debreczy、Benjamin Podányi、Géza Kereszturi、Mária Balogh、Ágnes Horváth、Péter Várkonyi

  DOI：10.3987/com-98-8143

  日期：——

  The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
• Anti-HIV diarylpyrimidine–quinolone hybrids and their mode of action
  作者：Tian-Qi Mao、Qiu-Qin He、Zheng-Yong Wan、Wen-Xue Chen、Fen-Er Chen、Gang-Feng Tang、Erik De Clercq、Dirk Daelemans、Christophe Pannecouque

  DOI：10.1016/j.bmc.2015.03.037

  日期：2015.7

  A molecular hybridization approach is a powerful tool in the design of new molecules with improved affinity and efficacy. In this context, a series of diarylpyrimidine-quinolone hybrids were synthesized and evaluated against both wt HIV-1 and mutant viral strains. The most active hybrid 5a displayed an EC50 value of 0.28 +/- 0.07 mu M against HIV-1 IIIB. A couple of enzyme-based assays clearly pinpoint a RT-targeted mechanism of action. Docking studies revealed that these hybrids could be well located in the NNIBP of HIV-1 RT despite the bulky and polar properties of a quinolone 3-carboxylic acid moiety in the molecules. (C) 2015 Elsevier Ltd. All rights reserved.
• Van Es, Theodorus; Staskun, Benjamin, South African Journal of Chemistry, 2002, vol. 55, p. 13 - 33
  作者：Van Es, Theodorus、Staskun, Benjamin

  DOI：——

  日期：——