6,7-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid | 103995-00-2

• 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: 6,7-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid
• 英文别名: 6,7-difluoro-1-(4-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• CAS: 103995-00-2
• 化学式: C₁₆H₉F₂NO₄
• 分子量: 317.249
• InChiKey: GSKFKYCVINLFOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  288-290 °C
• 沸点：
  547.6±50.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6,7-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 7-[(3S)-3-[(1R)-1-aminoethyl]pyrrolidin-1-yl]-6-fluoro-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  A Prodrug Approach toward the Development of Water Soluble Fluoroquinolones and Structure−Activity Relationships of Quinoline-3-carboxylic Acids

  摘要：

  A fluoroquinolone prodrug, PA2808, was prepared and shown to convert to the highly active parent drug PA2789. In vitro and in vivo activation of PA2808 by alkaline phosphatase was demonstrated using disk diffusion and rat lung infection models. The water solubility of PA2808 showed a marked increase compared to PA2789 over a pH range suitable for aerosol drug delivery. A total of 48 analogues based on PA2789 were prepared and screened against a panel of Gram-positive and Gram-negative pathogens. Incorporating a cyclopropane-fused pyrrolidine (amine g) at C-7 resulted in some of the most active analogues.

  DOI：

  10.1021/jm0497895
• 作为产物：
  描述：

  2,4,5-三氟苯甲酰氯 在 盐酸 、 乙酸酐 、 potassium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 103.67h， 生成 6,7-difluoro-1-(4-hydroxyphenyl)-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  A Prodrug Approach toward the Development of Water Soluble Fluoroquinolones and Structure−Activity Relationships of Quinoline-3-carboxylic Acids

  摘要：

  A fluoroquinolone prodrug, PA2808, was prepared and shown to convert to the highly active parent drug PA2789. In vitro and in vivo activation of PA2808 by alkaline phosphatase was demonstrated using disk diffusion and rat lung infection models. The water solubility of PA2808 showed a marked increase compared to PA2789 over a pH range suitable for aerosol drug delivery. A total of 48 analogues based on PA2789 were prepared and screened against a panel of Gram-positive and Gram-negative pathogens. Incorporating a cyclopropane-fused pyrrolidine (amine g) at C-7 resulted in some of the most active analogues.

  DOI：

  10.1021/jm0497895

文献信息

• [EN] COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS<br/>[FR] COMPOSÉS CIBLANT DES PROTÉINES DE LIAISON À L'ARN OU DES PROTÉINES MODIFIANT L'ARN
  申请人：TWENTYEIGHT SEVEN INC

  公开号：WO2021178420A1

  公开（公告）日：2021-09-10

  The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.

  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。
• Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid
  申请人：Otsuka Pharmaceutical Company Limited

  公开号：US04684648A1

  公开（公告）日：1987-08-04

  Novel 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R is hydrogen atom or fluorine atom, R.degree. is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, and X.sup.1 is hydrogen atom or fluorine atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.

  1-取代苯基-4-氧基喹啉-3-羧酸类化合物的分子式如下：其中R是氢原子或氟原子，R°是羟基、氟原子或具有1至6个碳原子的烷酰氧基，X^1是氢原子或氟原子，以及其药学上可接受的盐，这些化合物具有出色的抗微生物活性，因此可用作抗微生物剂，以及包含作为活性成分的该1-取代苯基-4-氧基喹啉-3-羧酸类化合物或其药学上可接受的盐与药学上可接受的稀释剂或载体混合而成的制药组合物。
• Antimicrobial 1-substituted Phenyl-4-oxoquinoline-3-carboxylic acid compounds
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0181521A1

  公开（公告）日：1986-05-21

  Novel compounds of the formula: wherein R1 is a group of the formula: (where R3 is hydrogen atom or an alkyl having 1 to 2 carbon atoms), or a group for the formula: R2 is a group of the formula: R4 is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, R5 is hydrogen or fluorine atom, and X is hydrogen or fluorine atom, provided that when R1 is and X is hydrogen atom, R2 is not a group of the formula and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said compounds or a salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.

  式的新型化合物，其中 R1 是式的基团：（其中 R3 是氢原子或具有 1 至 2 个碳原子的烷基），或式的基团：R2 是式的基团：R4 是羟基、氟原子或具有 1 至 6 个碳原子的烷酰氧基，R5 是氢原子或氟原子，X 是氢原子或氟原子，条件是当 R1 是且 X 是氢原子时，R2 不是式的基团及其药学上可接受的盐，所述化合物具有优异的抗菌活性，因此可用作抗菌剂，以及一种药物组合物，其活性成分包括与药学上可接受的稀释剂或载体混合的所述化合物或其盐。
• NISITANI, YASUXIRO;YAMAMOTO, SADAO
  作者：NISITANI, YASUXIRO、YAMAMOTO, SADAO

  DOI：——

  日期：——
• TONE, HITOSHI;MIYAMOTO, HISASHI;UEDA, HIRAKI;NAKAGAWA, KAZUYUKI
  作者：TONE, HITOSHI、MIYAMOTO, HISASHI、UEDA, HIRAKI、NAKAGAWA, KAZUYUKI

  DOI：——

  日期：——