光学活性取代的1,2-二氢-6-氧代-6H-吡咯并[3,2,1-ij]喹啉-5-羧酸的合成及抗菌活性
Synthesis and antibacterial activities of optically active substituted 1,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids.
作者信息
Tsuji K, Tsubouchi H, Ishikawa H
机构信息
Microbiological Research Institute, Otsuka Pharmaceutical Co., Ltd., Tokushima, Japan.
出版信息
Chem Pharm Bull (Tokyo). 1995 Oct;43(10):1678-82. doi: 10.1248/cpb.43.1678.
A series of optically active substituted 1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids was prepared via optically active 2-methyl-4,5-difluoroindoline (10) and tested for antibacterial activities. Among them, (2S)-9-[(3R,1'S)-3-(1'-amino)ethyl-1-pyrrolidinyl]-8-fluoro-1,2-dihydro- 2- methyl-6-oxo-6H-pyrrolo[3,2,1-ij]-quinoline-5-carboxylic acid (19) showed potent activity against gram-positive bacteria and (2S)-8-fluoro-1,2-dihydro-2-methyl-9-(3-methyl-1-piperazinyl)-6-oxo-6H- pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (16) exhibited well balanced in vitro activity, good intravenous efficacy, and high aqueous solubility.
通过旋光性的2-甲基-4,5-二氟吲哚啉（10）制备了一系列旋光性取代的1,2-二氢-6-氧代-吡咯并[3,2,1-ij]喹啉-5-羧酸，并对其抗菌活性进行了测试。其中，（2S）-9-[(3R,1'S)-3-(1'-氨基)乙基-1-吡咯烷基]-8-氟-1,2-二氢-2-甲基-6-氧代-6H-吡咯并[3,2,1-ij]喹啉-5-羧酸（19）对革兰氏阳性菌显示出强效活性，而（2S）-8-氟-1,2-二氢-2-甲基-9-(3-甲基-1-哌嗪基)-6-氧代-6H-吡咯并[3,2,1-ij]喹啉-5-羧酸（16）表现出体外活性良好、静脉给药效果良好以及高水溶性。
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