Enantioselective Synthesis of 2,8-Diazabicyclo[4.3.0]nonane Derivatives : Their Application to Quinolone Antibacterials
- 발행기관 고려대학교 대학원
- 발행년도 2004
- 학위명 박사
- 학과 대학원:화학과
- 식별자(기타) DL:000014913578
- 서지제어번호 000045213422
초록/요약
The quinolones have proven to be an important class of antibacterial agents whose mode of action involves inhibition of DNA gyrase. These agents have undergone hundreds of modifications over the last decade resulting in some very potent derivatives in various stages of clinical study. Recently, there are many possibilities to investigate and develop various substituents, because considerable increase of activity by optically pure substituents at C-7 position of quinolones. In this study, we have synthesized new optically pure (1S,4S,6R)-,(1R,4S,6S)-,(1S,4R,6R)-,(1R,4R,6S)-N,N-(tert-butoxycarbonyl)-4-methyl-2,8-diazabicyclo[4.3.0]nonane from N-(R-(+)-methylbenzyl)-3-ethoxycar bonyl-2,4-pyrrolidindione as a key intermediate. In a similar manner, (1S,6R)-N,N-(tert-butoxycarbonyl)-2,8-diazabicyclo[4.3.0]nonane and (1R, 6S)-N,N-(tert-butoxycarbonyl)-2,8-diazabicyclo[4.3.0]nonane have been synthesized, respectively. Further new quinolone antimicrobials agents could be synthesized by reaction of these new optically pure amine derivatives with various quinolone nucleuses, and those new quinolone derivatives should be able to be challenged to be new antimicrobial agents. The antibacterial activity for new quinolone derivatives is under investigation.
more목차
Ⅰ. 서 론
1. 연구 배경 ………………………………………………… 1
2. 결핵의 현황과 치료제의 개발 ………………………… 4
3. 연구 내용 및 목적 …………………………………… 9
II. 결과 및 고찰
1. 퀴놀론 모핵의 합성 ……………………… 12
2. 아민 유도체들의 합성 ……………………………… 16
3. In vitro 항균 활성 시험 ………………………………… 32
III. 결 론 …………………………………………… 34
IV. 실험 방법
1. 기기 및 시약 ……………………………………… 35
2. 실험 방법 ……………………………………… 36
V. 참고 문헌 ……………………………………… 68
Ⅵ. 부 록 …………………………………………… 70
