1-ethyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid | 119915-83-2

• 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: 1-ethyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 1-Ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-ethyl-6,7-difluoro-5-methyl-4-oxoquinoline-3-carboxylic acid
• CAS: 119915-83-2
• 化学式: C₁₃H₁₁F₂NO₃
• 分子量: 267.232
• InChiKey: NBBKNDJNGCEAQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-ethyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid 生成 1-ethyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  参考文献：
  名称：

  DOMAGALA, JOHN M.;HAGEN, SUSAN E.;KIELY, JOHN S.

  摘要：

  DOI：
• 作为产物：
  描述：

  1-bromo-2,4,5-trifluoro-6-methyl-3-(trimethylsilyl)benzene 在 盐酸 、 2,2'-联吡啶 、 正丁基锂 、 乙酸酐 、 sodium hydride 、 N,N-二甲基甲酰胺 、 cesium fluoride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.08h， 生成 1-ethyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  5-甲基-4-氧代喹啉羧酸的合成

  摘要：

  制备了一系列5-甲基-4-氧代-3-喹啉羧酸，其中八个位置被氟，氯，甲基或氢取代。这些喹诺酮是由衍生自恶唑啉8和16的合适的2-甲基-3,4,6-三氟苯甲酸合成的。恶唑啉部分既是邻位导向基团（在可行的情况下）又是保护基团；三甲基甲硅烷基部分被用来封闭分子中最酸性的位点。

  DOI：

  10.1002/jhet.5570270616

文献信息

• Benzoheterocyclic compounds
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US05290934A1

  公开（公告）日：1994-03-01

  Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.

  以下是翻译结果： 本发明涉及一种4-氧喹啉-3-羧酸化合物，其化学式为：##STR1## 其中，R1为环丙基，可能有1至3个烷基和卤素取代基；苯基，可能被1至3个烷氧基、卤素和羟基取代；烷基，可能被卤素、烷酰氧基或羟基取代；烯基；或噻吩基，R2为5至9个成员的饱和或不饱和杂环环，可能被取代，R3为烷基，R为氢或烷基，X为卤素，以及其药学上可接受的盐。该化合物具有优异的抗微生物活性，因此可用作抗微生物剂，以及含有该化合物作为活性成分的制药组合物。
• Intermediates for anti-microbial benzoheterocyclic compounds
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US05723648A1

  公开（公告）日：1998-03-03

  Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be sustituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.

  化合物的名称为Novel 4-oxoquinoline-3-carboxylic acid compounds，化学式为：##STR1## 其中，R.sup.1可以是环丙基，可以有1到3个烷基和卤素取代基；苯基，可以被1到3个烷氧基，卤素和羟基取代；烷基，可以被卤素，烷酰氧或羟基取代；烯基；或噻吩基，R.sup.2是5到9个成员的饱和或不饱和杂环环，可以被取代，R.sup.3是烷基，R是氢或烷基，X是卤素，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，还包括含有该化合物作为活性成分的制药组合物。
• Intermediates for anti-microbial quinolone carboxylic acids
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US05811576A1

  公开（公告）日：1998-09-22

  Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.

  公式：##STR1##其中R1是环丙基，可以有1至3个烷基和卤素的取代基；苯基，可以被1至3个烷氧基，卤素和羟基的取代基所取代；烷基，可以被卤素，烷酰氧基或羟基的取代基所取代；烯基；或噻吩基，R2是5至9个成员的饱和或不饱和杂环环，可以被取代，R3是烷基，R是氢或烷基，X是卤素，以及其药学上可接受的盐，这些化合物具有优异的抗微生物活性，因此可用作抗微生物剂，以及含有该化合物作为活性成分的制药组合物。
• Antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0326891A2

  公开（公告）日：1989-08-09

  Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  介绍了作为抗菌剂的新型萘啶酸和喹啉羧酸及其制造、配制和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体。
• Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids
  作者：Susan E. Hagen、John M. Domagala、Carl L. Heifetz、Judith Johnson

  DOI：10.1021/jm00107a040

  日期：1991.3

  A series of 5-alkyl-1,7,8-trisubstituted-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids was prepared and evaluated for in vitro and in vivo antibacterial activity. When compared to the 5-hydrogen analogues, the presence of the 5-methyl group enhanced in vitro potency for those compounds containing a cyclopropyl moiety at N1 but decreased potency for those containing an ethyl group at N1. Replacing the 5-methyl with a 5-ethyl significantly reduced the efficacy. In general, the 5-methyl and 5-hydrogen analogues were equipotent in vivo. Several of the 5-methyl-1-cyclopropylquinolones displayed excellent in vitro and in vivo activity, warranting further development.