Studies on the Synthesis of Pterdine Substituted Pyridonecarboxylic Acids as Potential Antibacterial Agents and their Antimicrobial Activities

항균제로서 Pteridine이 치환된 Pyridonecarboxylic Acids의 합성 및 항균 작용에 관한 연구

  • 류성렬 (대불대학교 화학공학과) ;
  • 주동준 (경희대학교 문리과대학 화학과)
  • Received : 1996.07.20
  • Accepted : 1996.11.15
  • Published : 1996.12.10

Abstract

In order to synthesize a new antibacterial and antitumor agents, we have prepared new analogues pteroic acid(13a, 13b), which means C-9 position of pteroic acid has been replaced by norfloxacin(8) or ciprofloxacin(9) and amino group of C-2 position by $CH_3$. These derivatives were synthesized coupling at N-4 piperazine of norfloxacin and ciprofloxacin with 2-amino-3-cyano-5-chloromethylpyrazine(20) provided 1-alkyl(ethyl, cyclopropyl)-6-fluoro-1,4-dihydro-4-oxo-7-[[4-N-(2-amino-3-cyanopyrazin-5-yl)methyl]piperazin-1-yl]-3-quinoline-carboxylic acid(12a, 12b). It was then cyclized with acetamidine. HCI to obtain new analogues of C-2 desaminomethylpteroic acid(13a, 13b) in yield of 76.2% and 82.8 % respectively. These compounds were tested in vitro on antibacterial activity against Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa ATCC9027. In general, these synthesized compounds(13a, 13b) showed less potent activities than those of norfloxacin.

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