약학회지 (YAKHAK HOEJI)

  • 제42권1호
  • /
  • Pages.12-24
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  • 1998
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  • 0377-9556(pISSN)
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  • 2383-9457(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

3- (치환) 테트라조일메칠세파로스포린의 합성과 생리활성

Synthesis and Biological Activity of 3 - (Substituted) Tetrazolylmethyl Cephalosporins

  • 발행 : 1998.02.01
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초록

For the development of new cephalosporin antibiotics with aminothiazolcarboxymethylethoxyimino moiety on the C-7 position and tetrazolymethyl moiety on the C-3 position of cephe m ring, 7${\beta}$-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[5-(substituted)tetrazol-2-yl]methyl-3-cephem-4-carboxylic acids(28-35) were synthesized. These compounds were tested for antimicrobial activity in vitro against Gram(+) and Gram(-) bacteria. They showed remarkable antibacterial activity against Escherichia coli AB 1157, Escherichia coli AB 0111, Escherichia coli BE 1186, Micrococcus luteus ATCC 9341, Salmonella typhimurium TV 119, Salmonella typhimurium SL 1102, Staphylococcus aureus IFO 12732, Staphylococcus aureus R-209, but these compounds were not active against Pseudomonas aeruginosa N-10.

키워드

참고문헌

  1. Current chemotheraphy and infectious disease v.Ⅰ Ceftizoxime (FK 749)). a new paranteral cephalosporin : in vitro and in vivo antibacterial activities Takaya, T.;Kamimura, T.;Kojo, H.;Mine, Y.;Nishida, S.;Goto, S.;Kuwahara, S.
  2. Nippon Kagaku Kaishi v.1981 Structure-activity relationships of sodium 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylate(ceftizoxime) and its related compounds Takaya, T.;Takasugi, H.;Masugi, T.;Chiba, T.;Kochi, H.;Takano, T.;Nakano, H.
  3. J. Antibiotics v.34 Studies on β-lactam antibiotics. Ⅳ. Structure-activity relationships of 7β-[⑵-2-alkoxymino-2-(2-amino-4-thiazolyl) acetamido]-3-cephem-4-carboxylic acids Takaya, T.;Takasugi, H.;Masugi, T.;Kochi, H.;Nakano, H.
  4. C. R. Acad. Sci. Paris. Serie D. v.284 Properties antibiotiques inattendues dans le domains des cephalosporins Bucourt, R.;Heymes, R.;Lutz, A.;Penasse, L.;Perronnet, J.
  5. Infection v.5 Experimental evaluation of HR 756. a new cephalosporin derivative : Pre-clinical study Heymes, R.;Lutz, A.;Schrinner
  6. Chem. Pharm. Bull. v.25 New cephalosporin derivatives with high antibacterial activities Ochiai, M.;Aki, O.;Morimoto, A.;Okada, T.;Matsushita, Y.
  7. J. Antibiotics v.33 Ro 13-99041001, a novel potent and long-acting parenteral cephalosporin Reiner, R.;Welss, U.;Brombacher, U.;Lanz, P.;Montavon, M.;Furlenmeier, A.;Angehrn, P.;Probst, P. J.
  8. J. Antibiotics v.38 Synthesis and biological activity of a new orally active cephalosporin, Cefixime (FK 027) Yamanaka, H.;Chiba, T.;Kawabata, K.;Takasugi, H.;Masugi, T.;Takaya, T.
  9. Antimicrob. Agents Chemother v.17 A new aminothiazoyl cephaosporin with high activity against Pseudonas and Enterobacteriaceae Ocallaghan, C. H.;Acred, P.;Harper, P. B.;Ryan, D. M.;Kirby, S. M.;Harding, S. M.
  10. J. Med. Chem. v.22 no.10 Comparative cytotoxic and biochemical effects of ligands and metal comlexes of α-N-heterocyclic carboxaldehyde thiosemicarbazones Saryan, L. A.;Ankel, E.;Krishnamurti, C.;Petering, D. H.;Elford, H.
  11. J. Med. Chem. v.22 no.10 3-[(1,2,3-thiadiazol-5-ylthio) methyl] cephalosporins Lewis G. S.;Nelson P. H.
  12. J. Antibiotics v.39 no.9 Semisynthetic β-lactam antibiotics Ⅲ. Synthesis and antibacterial activity of 7β-[2-(2-aminothiazol-4-yl)-2-(substituted carbamoyl methoxyimino) acetamido]cephalosporins Arimoto, M.;Hayano, K.;Soga, T.;Yoshioka, T.;Tagwa, H.;Furukawa, M.
  13. J. Antibiotics v.47 no.4 Studies on β-lactam antibiotics Ⅳ. An improved synthesis of 3-(isothiazolyl-thiomethyl) cephalosporins and its application to new derivatives Hara, R.;Nakai, E. I.;Hiasmichi, H.;Nagano, N.
  14. J. Antibiotics v.48 no.5 Structure-activity relationships within a series of C⑺-substituted doxyiminocephalosporins containing the C⑶-Synthesis and biological properties of BRL 57342 and some close analogues Adams, R. G.;Brain, E. G.;Branch, C. L.;Guest, A. W.;Harrigton, F. P.;Mizen, L.;Neale, J. E.;Pearson, M. J.;Simson, I. N.;Smulders, H.;Zomaya, I. I.
  15. J. Antibiotics v.XLI no.12 Semisynthetic β-lactam antibiotics Ⅳ. Synthesis and antibacterial activity of 7β-[2-(heteroaromatic methoxyimino)-2-(2-amino-thiazol-4-yl) acetamido] cephalosporins Arimoto, M.;Yokohama, S.;Sudov, M.;Ichikawa, Y.;Hayano, T.;Tagawa, H.;Furukawa, M.
  16. J. Antibiotics v.XLI no.10 Synthesis and structure-activity realationships in the cefpirome series Ⅱ. Analogues of cefpirome with different 7-heteroaryl-acetamido and 3'-ammonium substituents Lattrell, R.;Blumbach, J.;Ckheimer, W.;Schmann, K. F.;Kirrstetter, R.;Klesel, N.;Mencke, B.;Scheunemann, K. H.;Schwab, W.;Seliger, H.;Stache, U.;Winkler, I.
  17. J. antibiotics v.44 no.12 Studies on condensed-heterocyclic azolium cephalosporins Ⅱ. Synthesis and antibacterial activity of 7β-[2-(2-aminothiazole-4-yl)-2(Z)-alkoxyiminoacetamido]-3-(condensed-heterocyclicazolium)methyl-3cephem-4-carboxylates Yoshimura, Y.;Miyake, A.;Nishimura, T.;Kawai, T.;Yamaoka, M.
  18. J. antibiotics v.45 no.4 Studies on condensed heterocyclic azolium cephalosporins Ⅲ. Synthesis and antibacterial activity of 7β-[2-(2-amino-5-substituted-thiazole-4-yl)-2(Z)-alkoxyiminoacetamido]-3-(condensed-heterocyclic azolium) methyl-3-cephem-4-carboxylates Nishimura, T.;Yoshimura, Y.;Miyake, A.
  19. Korean J. Med. Chem. v.3 no.1 Synthesis and biological activities of 3-(dihydroxycin-namamidoalkyl) pyridiniummethyl cephalosporins Cho, S. K.;Lee, K. H.;An, S. H.
  20. J. Antibiotics v.46 no.2 FK037. A new parenteral cephalosporin with a broad antibacterial spectrum: Synthesis and antibacterial activity Ohki, H.;Kawabata, K.;Okuda, S.;Kamimura, T.;Sakane, K.
  21. J. Antibiotics v.48 no.8 Structure-antivity realtionships of 2-thiosocephem against methicillin resistant Staphylococcus aureus Hanaki, H.;Akagi, H.;Yasui, M.;Otani, T.
  22. J. Antibiotics v.48 no.9 Studies on 3'-quaternary ammonium cephalosporins Ⅱ. Synthesis and antibacterial activity of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] cephalosporin derivatives bearing various quaternary ammonium methyl groups at the 3 position Ohki, H.;Kawabata, K.;Okuda, S.;Kamimura, T.;Sakane, K.
  23. J. Antibiotics v.49 no.12 Synthesis and biological activity of quaternary ammonioprop-enylcephalosporins with hydroxylated alicyclic or aliphatic amines Lee, J. Y.;Lee, Y. S.;Suk, D. W.;Woo, E. R.;Chung, B. Y.;Park, H, K.
  24. J. Antibiotics v.38 no.12 Studies on β-lactam antibiotics Ⅸ. Synthesis and biological activity of a new orally active cephalosporin, cefixime(FK 027) Yamanaka, H.;Chiba, T.;Kawabata, K.;Takasugi, H.;Masugi, T.;Takaya, T.
  25. J. Antibiotics v.39 no.3 Studies on β-lactam antibiotics XI. Synthesis and structure-activity realationships of new 3-(2,2-dihalovinyl) cephalosporins Kawabata, K.;Masugi, T.;Takaya, T.
  26. J. Antibiotics v.39 no.3 Studies on β-lactam antibiotics XIII. Synthesis and structure-activity relationships of 7β-[(Z)-2-aryl-2-carboxymethoxyiminoacetamido]-3-vinylcephalosporins Kawabata, K.;Yamanaka, H.;Takasugi, H.;Takaya, T.
  27. J. Antibiotics v.48 no.1 Synthesis and biological acitivity of novel cephalosporins containing a (Z)-vinyl dimethylphosphonate group Smith, P. W.;Chamiec, A. J.;Chung, G.;Cobley, K. N.;Duncan, K.;Howes, P. D.;Whittigton, A. R.;Wood, M. R.
  28. J. Antibiotics v.49 no.11 Structure-activity relationships of cephalosporins having a (dimethylisozazoli-dinio)vinyl moiety at their 3-position Hara, R.;Sakamoto, K.;Hisamichi, H.;Nagano, N.
  29. J. Antibiotics v.49 no.11 Cycloaddition reactions of a 3-(1,3-butadienyl) cephalosporin and antibacterial activity of new cephem derivatives Hara, R.;Itahana, H.;Sakamoto, K.;Hisamichi, H.;Nagano, N.
  30. J. Antibiotics v.39 no.8 Synthesis and Structure-activity relationships of a new series of cephalosporins. BMY-28142 and related compounds Naito, T.;Aburaki, S.;Kamachi, H.;Narita, Y.;Okumura, J.;Kawaguchi, H.
  31. J. Med. Chem. v.35 no.14 Synthesis Structure-activity relationships of cephlosporins with C-3' catechol-containing residues Arnould, J. C.;Bertrandie, A.;Bird, T. G. C.;Boucherot, D.;Jung, F.;Lohmann, J. J.;Oliver, A.;Bailey, J. P.;Bell, W.;Davies. G. M.
  32. Korean J. Med. Chem. v.3 no.1 Synthesis and biological activities of 3-(dihydroxy-cinnamamidoalkyl) pyridiniummethyl cephalosporins Cho, S. K.;Lee, K. H.;An, S. H.
  33. Korean J. Med. Chem. v.3 no.1 Synthesis and biological activity of 3-(dioxopiperazinylcarboxyamido) pyridinium mehtyl cephalosporins Cho, S. K.;Yoon, Y. H.;Lee, K. H.;An, S. H.;Kim, C. S.
  34. J. Antibiotics v.48 no.3 Novel cephalosporins having a benzothiopyran group 2. Synthesis and biological activity of catecholic benzothiopyran group at the C-3 side chain Obi, K.;Saito, T.;Kojima, A.;Fukuda, H.;Hirai, K.;Suzue, S.
  35. J. Antibiotics v.49 no.5 Synthesis and antibacterial activites of novel C⑺-catechol-substituted cephalosporins(Ⅱ) Kim, Y. Z.;Lim, J. C.;Yeo, J. H.;Bang, C. S.;Kim, S. S.;Lee, T. H.;Oh, S. H.;Moon, Y. C.;Lee, C. S.
  36. J. Antibiotics v.49 no.11 Synthesis and biological activity of new cephem compounds with a 3-(2-butenyl) and a 3-(1,3-butadienyl)group at their 3-position Hara, R.;Itahana, H.;Hisamichi, H.;Fukuoka, S.;Nagano, N.
  37. J. Antibiotics v.50 no.3 Studies on new catechol containing cephalsporins having a pyridone moiety at the C-7 position Choi, K. I.;Cha, J. H.;Pae, A. N.;cho, Y. S.;Koh, H. Y.;Chang, M. H.;Kang, H. Y.;Chung, B. Y.
  38. J. Antibiotics v.44 no.10 Synthesis and biological activity of novel 3-(2-propenyl) cephalosporin Ⅱ. Preparation of prodrugs Kim, W. J.;Ko, K. Y.;Jung, M. H.;Kim, M. H.;Lee, K. Y.;Kim, J. H.
  39. Yakhak Hoeji v.37 no.3 Synthesis and antibacterial activities of new oral cephalosporins La, S. B.;Jung, M. H.;Kim, W. J.;Jee, U. K.
  40. ARch. Pharm. Res. v.17 no.2 Synthesis and antibacterial activity of new cephalosporins with lactonyloxyimino moiety Suh, K. H.;Park, J. W.