2-取代-6-氧代-8-氟-9-喊氮杂环-6H-咪唑并(4,5,1-ij)-喹啉-5羧酸及其类似物的合成和抗菌活性

2-取代-6-氧代-8-氟-9-喊氮杂环-6H-咪唑并(4,5,1-ij)-喹啉-5羧酸及其类似物的合成和抗菌活性

周伟澄, 刘庆, 徐振宇, 余爱珍, 张秀平

上海医药工业研究院, 上海 200437

收稿日期:1997-02-26 修回日期:1997-06-18 出版日期:1998-06-15 发布日期:1998-06-15

Synthesis and Antibacterial Activities of 2-Substituted-6-oxo-8-fluoro-9-nitrogen-containing Heterocycle-6H-imidazo(4,5,1-ij)-quinoline-5-carboxylic Acids and Their Analogues

Wei-Cheng Zhou, Qing Liu, Zhen-Yu Xu, Ai-Zhen Yu, Xiu-Ping Zhang

Shanghai Institute of Pharmaceutical Industry; Shanghai 200437

Received:1997-02-26 Revised:1997-06-18 Online:1998-06-15 Published:1998-06-15

摘要/Abstract

摘要： 6-氟-7-(4-甲基-1-哌嗪基)-8-氨基-4-氧代-1,4-二氢喹啉-3-羧酸乙酯(5A) 和脂肪酸在PPA中缩合,得2-烃基-6-氧代-8-氟-9-(4-甲基-1-哌嗪基)-6H-咪唑并(4, 5, 1-ij) 喹啉-5-羧酸(2Ab~2Ae), 6-氟-7-含氮杂环-8-氨基-4-氧代-1, 4-二氢-3-喹啉羧酸(9A~9D) 与各种酸在PPA中缩合或与原甲酸三乙酯缩合或经重氮化反应, 可分别得到其它目的物2Af~2Ah, 2Bc, 2Cc, 2Aa~2Da, 2Bi 和2Ci。体外抗菌筛选证明仅化合物2Ab和2Ac 具有中等程度的抗菌作用。

关键词: 氟喹诺酮, 咪唑并喹啉, 抗菌剂

Abstract: 2-Alkyl-6-oxo-8-fluoro-9-(4-methylpiperazin-1-yl)-6H-imidazo(4,5,1-ij)-quino-line-5-carboxylic acids (2Ab~2Ae) were prepared by condensation of ethyl 6-fluoro-7-(4-meth-ylpiperazin-1-yl)-8-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylate (5A) with the aliphatic acids in PPA. Other target compounds 2Af~2Ah, 2Bc, 2Cc, 2Aa~2Da, 2Bi and 2Ci were prepared by the condensation of 6-fluoro-7-nitrogen-containing heterocycle-8-amino-1,4-dihydro-4-oxo-3-quinoline-carboxylic acids (9A~9D) with the corresponding acids in PPA or with ethyl ortho-formate or by the diazotisation of 9B and 9C, respectively. Only 2Ab and 2Ac showed moderate antibacterial activity in in vitro test.

Key words: Fluoroquinolones, Imidazoquinolines, Antibacterials

Supporting: ^*Supported by Nation New Drug Foundation of China No: 93-41-N-19.

周伟澄, 刘庆, 徐振宇, 余爱珍, 张秀平. 2-取代-6-氧代-8-氟-9-喊氮杂环-6H-咪唑并(4,5,1-ij)-喹啉-5羧酸及其类似物的合成和抗菌活性[J]. .

Wei-Cheng Zhou, Qing Liu, Zhen-Yu Xu, Ai-Zhen Yu, Xiu-Ping Zhang. Synthesis and Antibacterial Activities of 2-Substituted-6-oxo-8-fluoro-9-nitrogen-containing Heterocycle-6H-imidazo(4,5,1-ij)-quinoline-5-carboxylic Acids and Their Analogues[J]. .