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The Pharmaceutical Society of Korea (대한약학회)
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Synthesis and Antimicrobial Activities of Some New Nitroimidazole Derivatives

  • Benkli, Kadriye (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu) ;
  • Karaburun, Ahmet-Cagrl (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu) ;
  • Gundogdu-Karaburun, Nalan (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu) ;
  • Demirayak, Seref (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu) ;
  • Guven, Klymet (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
  • Published : 2003.10.01
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Abstract

In this study, some new nitroimidazole derivatives were obtained from 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylamine dihydrochloride (4) and 1-(2-bromoethyl)-2-methyl-5-nitroimidazole (5), which were prepared using metronidazole. Compound 4 was reacted with arylisothiocyanates (6) to obtain 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-3-arylthioureas (7) and the latter with $\alpha$-bromoacetophenones (8) to give -3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-arylimino-4-aryl-4-thiazolines (9). Also 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-phenyl-4-arylideneimidazolin-5-ones (11) were prepared by reaction of 4 with 2-phenyl-4-arylidene-5-oxazolones (10). The reaction of the other starting material 5 with 5-arylidenethiazolidin-2,4-dione (12) gave 3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-5-arylidenethiazolidin-2,4-dione (13) derivatives. Structural elucidation of the compounds was performed by IR, $^1H-NMR$ and MASS spectroscopic data and elemental analysis results. Antimicrobial activities of the compounds were examined and moderate activity was obtained.

Keywords

References

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