새로운 베타락탐 항생물질의 합성과 생물활성에 관한 연구

Studies on the Synthesis and Antibacterial Activity of New $\beta$-Lactam Antibiotics

  • 송태흥 (세종대학교 자연과학대학 화학과) ;
  • 김영호 (세종대학교 자연대학 화학과)
  • Tae Heung Song (Department of Chemistry, King Se-jong University) ;
  • Young Ho Kim (Department of Chemistry, King Se-jong University)
  • 발행 : 1992.04.20

초록

신규 cephalosporin계 항생제로서, 7-[(Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido]-3-(4,6-diamino-1-alkyl-1,3,5-triazinium-2-yl)thiomethyl-3-cephem-4-carboxylate의 유도체들을 합성하였다. 7-위치의 side chain에 있는 oxyimino 부위를 변화시켜서, 구조 변화에 따른 항균 활성의 변화를 측정하였다. 그 결과, 3-위치에서 4,6-diamino-1-methyl-1,3,5-triazinium-2-yl group을 가지며, 또한 7-$\alpha$-methoxyimino기를 가진, C-1유도체가 가장 강력하고도 광범위한 항균활성을 그람 양성과 그람 음성 bacteria에 대하여 나타내었다.

The synthesis of a series of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido]-3-(4,6-diamino-1-alkyl-1,3,5-triazinium-2-yl)thiomethyl-3-cephem-4-carboxylates is described. Variations of an oxyimino moiety in the 7-side chain and quaternary ammonium moiety in the 3-side chain were examined and structure-activity relationship was studied. The 4,6-diamino-1-methyl-1,3,5-triazinium-2-yl derivative of the 7-$\alpha$-methoxyimino series of cephalospoins, particularly 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(4,6-diamino-1-methyl-1,3,5-triazinium-2-yl)thiomethyl-3-cephem-4-carboxylate(C-1), exhibited broad antibacterial activity against Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa.

키워드

참고문헌

  1. Proc. 10th Intern. Congr. Chemother v.2 R. Heymes;A. Lutz;E. Schrinner
  2. Angew. Chem. Int. Ed. Engl. v.24 D. Walter;J. Blumbach;R. Lattrell;K. H. Schenuemann
  3. Tetrahedron. v.34 R. Bucourt;R. Heymes;A. Lutz;L. Perasse;J. Peronnet
  4. Preceedings, 13th int. Congress of Chemotherapy(13th ICC) v.4 R. Latterel;W. Durkheimer;R. Kirrstetter(et al.)
  5. J. Antibiol. v.43 S. Seiji;O. Tsuneo;Y. Takashi;M. Yasushi(et al.)
  6. J. Indian Chem. Soc. v.66 no.5 S. Miss;E. Tyagi;R. L. Mital(et al.)
  7. Drugs of the Future v.5;6
  8. J. Antibiol. v.36 H. Takasugi;H. Kochi;T. Masugi;H. Nakano;T. Takaya
  9. J. Antibiol. v.33 R. Reiner;U. Weiss;U. Brombacher;P. Lanz;M. Montavon;A. Furlenmeier;P. Angehrn;P. J. Probst
  10. J. Antibiol. v.37 M. Limbert;N. Klessel;K. Seeger;G. Seibert;I. Winkler;E. Schrinner
  11. J. Antibiol. v.36 W. V. Curran;A. A. Ross
  12. Drugs of the Future v.9
  13. J. Antibiol. v.41 R. Lattrell;J. Blumbach;W. Duerckheimer(et al.)
  14. Tetrahedon v.34 Bucourt;R. R. Heymes;A. Lutz;L. Penasse;J. Perronnet
  15. J. Chem. Soc. F. Kurtzer;E. D. Pitchfork