YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

A Study on the Synthesis and Antibacterial Activities of 3-[(4-Carboxy-5-ethylthioisothiazo1-3-yl) oxymethyl] cephalosporin Derivatives

3-[(4-카르복시-5-레틸티오이소티아졸-3-일)옥시메틸] 세파로스포린 유도체들의 합성 및 항균력에 관한 연구

  • 최원식 (순천향대학교 자연과학대학 생명과학부) ;
  • 박의석 (순천향대학교 자연과학대학 생명과학부) ;
  • 박규종 (원광대학교 자연과학대학 화학과) ;
  • 이영행 (원광대학교 자연과학대학 화학과)
  • Published : 2000.04.01
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Abstract

New cephalosporin antibiotics , 3-[(4-carboxy-5-ethylthioisothiazol-3-yl)oxymethyl]-7-[(1H-tetra-zol-1-yl)acetamido]-3-cephem-4-carboxylic acid 2, 3-[(4-carboxy-5-ethylthioisothiazol-3-yl) oxymethyl]-7-[(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid 3, 3-[(4-carb oxy-5-ethylthioisothiazol-3-yl)-oxymethyl]-7-[5-(ethylthio-3-hydroxyisothiazol-4-yl)carboxamido]-3-cephem-4-carboxylic acid 4, 3-[(4-car-boxy-5-ethylthioisothiazo1-3-yl)oxymethy1]-7-[(Z)-2-(fur-2-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid 5, 7-[(Z)-2-(2-aminothiazol-4-yl)-2-[(alkoxyimino)acetamido]-3-[(4-carboxy-5-ethylthioisothiazol-3-yl)oxymethyl]-3-cephem-4-carboxylic acid 6-8 were synthesized. Antibacterial activities and structure-activity relationships of these new cephalosporin derivatives were examined. Among them, 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(4-carboxy-5-ethylthylth-ioisothiazol-3-yl)oxymethyl]-3-cephem-4-carboxylic acid 7 exhibited good antibacterial activities compared to cefotaxime and ceftriaxone.

Keywords

References

  1. In Recent Advance in the Chemical of β-Lactam Antibiotics 1st ed Gregory,G.I
  2. J.Org.Chem v.53 Use of Biotrimethylsiylated In-termediates in the Preparation of Semisynthetic 7-Amino-3-Substituted cephems Walker,D.G Brodfuehrer,P.R.,Shim,K.M.;Sapino,C
  3. Cephalos-porin Antibiotics.J.Antibiot Nakayama,E.Watanabe,K.,Miyauchi,M.,Fuj-imoto,K.Muramatsu,S.;Ide,J
  4. Cephalosporin Antibiotics.J.Antibiot v.44 Nakauyama,E.Watanabe,K.,Miyauchi,M.Fujimoto,K.,Muramatsu,S.,Uasuda,H.;Fuji-moto,M
  5. Studies on 3'-Quaternary Ammonium Cephalosporins.J.Antibiot v.48 Hidenori,O.kawabata,K.Okuda,S.,Kamimura,T.;Sakane,K
  6. Synthesis and Antibacterial Activites of Novel Cephalosporins.J.Antibiot v.41 Kosuzume,H.
  7. Synthesisand Antibacterial Activities of Novel C(7)-Cathechol-substituted Cephalosporins(Ⅱ).J.Antibiot v.49 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.H.
  8. J.Antibiot v.48 Structure-Activity Relationships within a Series of C(7)-Substitued oxyiminocephalosporins Containing the C(3)-Methylaminopyriniumthiomethyl Substi-tuent Adams,R.G.,Edward,G.B.,Clive,L.B.,Angela,W.G.,Frank,P.H.,Linda,M.,Jane,E.N;Michael,J.P
  9. Drug fut v.13 no.1
  10. Ibid v.15
  11. Novel Cephalosporins Havig a Benzo-thiopyran Group 2.J.Antibiot v.48 Obi,K.,Saito,T.Kohima,A.,Fukuda,H.Hirai,K.;Suzue,S.
  12. Studies on β-Lactam Antibiotics.J.Antibiot v.38 Yamanaka,H.,Chiba,T.Kawabata,K.,Takasugi,H.,Masugi,T.;Takaya,T
  13. Studies on β-Lactam Antibiotics.J.Antibiot v.39 Yamanaka,H.,Kawabata,K.,Miyai,K.,Takasugi,H.,Kamimura,T.,Mine,Y.;Takaya,T
  14. Cephalosporin Antibiotics.J.Antibiot v.44 Nakayama,E.,Fugimoto,K.,Muramatsu,S.,Miyauchi,M.,Watanabe,K.;Ide,J
  15. J.Antibiot v.44 Kim,W.J.,Ko.K.Y.,Kim,H.B.;Oh,J.H.
  16. Chem.Pham,Bull v.28 Iwanami,M.T.Maeda,M.Fujimoto,Y.Nagano,N.Nagano,A.Yamazaki,T.Shibanuma;Tamazawa,K