ethyl 6,7-difluoro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylate | 108138-15-4

• 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 6,7-difluoro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 6,7-difluoro-4-oxo-1-phenylquinoline-3-carboxylate
• CAS: 108138-15-4
• 化学式: C₁₈H₁₃F₂NO₃
• 分子量: 329.303
• InChiKey: GBOPMRPUZZWCTO-UHFFFAOYSA-N

物化性质

• 沸点：
  457.8±45.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6,7-difluoro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylate 在 水 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (R)-6-fluoro-7-(2-(((3-methylpyridin-2-yl)oxy)methyl)pyrrolidin-1-yl)-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS
  [FR] COMPOSÉS CIBLANT DES PROTÉINES DE LIAISON À L'ARN OU DES PROTÉINES MODIFIANT L'ARN

  摘要：

  该发明涉及由化学式（I）表示的化合物，或其药用可接受盐，包括含有该化合物的组合物以及制备和使用该化合物的方法。这里描述了变量。

  公开号：

  WO2021178420A1
• 作为产物：
  描述：

  2,4,5-三氟苯甲酰乙酸乙酯 在 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 6,7-difluoro-4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria

  摘要：

  The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms. As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenylsubstituted derivatives to explore the effect of increasing lipophilicity on potency at this position. The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pK(a), and other attributes. The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M, tuberculosis activity. The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria. Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.

  DOI：

  10.1021/jm00015a021

文献信息

• Advantageous Use of Ionic Liquids for the Synthesis of Pharmaceutically Relevant Quinolones
  作者：Rolando Cannalire、Matteo Tiecco、Violetta Cecchetti、Raimondo Germani、Giuseppe Manfroni

  DOI：10.1002/ejoc.201800415

  日期：2018.6.22

  The use of ILs instead of DMF in the Grohe cycloaracylation for the synthesis of pharmaceutically relevant quinolones has several advantages. [TBMA][MsO] was the most favourable IL and was used in a one‐pot/three‐step procedure for the preparation of a quinolone acid by a totally green procedure. Our procedure represents an alternative approach to the industrial production of quinolones.

  在Grohe环酰化反应中使用IL代替DMF合成药物相关喹诺酮具有若干优势。[TBMA] [MsO]是最有利的IL，用于一锅/三步程序中，通过完全绿色的程序制备喹诺酮酸。我们的程序代表了喹诺酮类工业生产的替代方法。
• US4956465A
  申请人：——

  公开号：US4956465A

  公开（公告）日：1990-09-11