Journal of Life Science (생명과학회지)

Korean Society of Life Science (한국생명과학회)
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Syntheses and Antibacterial Activities of New Quinolones Containing cis- or trans-3-Amino-4-methylthiomethylpyrrolidino Moiety

시스 또는 트란스-3-아미노-4-메틸티오메틸피롤리디닐기를 포함하는 퀴놀론 항균물질의 합성과 효능검색

  • Published : 2003.12.01
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Abstract

New quinolone derivatives of 7-(cis- or trans-3-amino-4-mehtylthiomethylpyrrolidinyl) quinolone-3-carboxylic acids were synthesized by condensation of 7-halo substituted quinolone-3-carboxylic acids with cis- or trans-3-amino-4-mehtylthiomethylpyrrolidine. Some of these compounds showed broad spectra of antibacterial activities against Gram-positive and Gram-negative organisms except Pseudomonas aeruginosa, and exhibited much stronger activity against MRSA.

7번 위치에 하롤겐이 치환된 여로종류의 퀴놀론 모핵과 시스 또는 트란스-3-아미노-4-메틸오메틸피롤리딘을 반응시켜 7-(시스 또는 트란스-3-아미노-4-메틸티오메틸피롤리디닐) 퀴롤론-3-카르복실산의 신규 항균제를 합성하였다. 새롭게 합성된 퀴놀론의 약효는 그람양성균에 대해 대조물질인 시프로플로삭신보다 매우 탁월하였고, 녹농균이외의 그람음성균에 대해서도 대조물질과 거의 유사하였다. 그리고 임상에서 문제가 되고 있는 메티실린 내성 포도상구균(MRSA)에 대한 신규 퀴놀론의 약효는 더욱더 향상되어진 것으로 나타났다.

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References

  1. J. Med. Chem. v.33 New quinolone antibacterial agents. Synthesis and biological activity of 7-(3,3- or 3,4-disubstituted-1-pyrrolidinyl)quinoline-3-carboxylic acids Hagen,S.E.;J.M.Domagala;C.L.Heifetz;J.P.Sanchez;M.Solomon https://doi.org/10.1021/jm00164a060
  2. Quinolones Antimicrobial Agents(2nd eds.) Hopper,D.C.;J.S.Wolfson
  3. Kor. J. Med. Chem. v.4 Synthesis and antibacterial activities of quinolones containing 3-amino-4-methylthiomethyl-pyrrolidine at the 7-position Lee,J.W.;H.J.Son;K.S.Lee;M.H.Park;B.O.Kim
  4. Yakhak Hoeji v.38 Synthesis and antimicrobial activity of 7-[(3-methylthio or 3-methylthiomethyl)pyrrolinyl]quinolone-3-carboxylic acids Lee,J.W.;H.J.Son;K.S.Lee;Y.H.Yu;D.Y.Kim
  5. Yakhak Hoeji v.38 Synthesis and antimicrobial activity of 7-[3-hydroxy-(4-methylthio or 4-methylthiomethyl)pyrrolinyl]quinolone-3-carboxylic Acids Lee,J.W.;H.J.Son;K.S.Lee;Y.H.Yu;G.J.Yoon
  6. J. Med. Chem. v.30 Pyridonecarboxylic acids as antibacterial agents. Synthesis and antibacterial activity of 1-substituted 6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylic acids Nishimura,Y.;J.Matsumoto https://doi.org/10.1021/jm00392a017
  7. J. Med. Chem. v.31 Asymmetric synthesis and properties of the enantiomers of the antibacterial agent 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride Rosen,T.;D.T.W.Chu;I.M.Lico;P.B.Fernandes;L.Shen;S.Borodkin;A.G.Pernet https://doi.org/10.1021/jm00403a017
  8. J. Med. Chem. v.31 Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids Sanchez,J.P.;J.M.Domagala;S.E.Hagen;C.L.Heifetz;M.P.Hutt;J.B.Nichols;A.K.Trehan https://doi.org/10.1021/jm00400a016
  9. J. Med. Chem. v.30 Synthesis of antimicrobial agents. 1. Syntheses and antibacterial activities of 7-(azole substituted)quinolones Uno,T.;M.Takamatsu;Y.Inoue;Y.Kawahata;K.Iuchi;G.Tsukamoto https://doi.org/10.1021/jm00395a001
  10. J. Org. Chem. v.26 Pyrrolidinediols. 1-Substituted 3-hydroxymethyl-4-hydroxypyrrolidines and derivatives Wu,Y.H.;R.F.Feldkamp https://doi.org/10.1021/jo01064a051