Synthesis and antimicrobial activities of some new nitroimidazole derivatives.
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.
Benkli
Kadriye
K
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu, 26470 Eskişhir, Turkey. kbenkli@anadolu.edu.tr
Karaburun
Ahmet Cağri
AC
Gündoğdu-Karaburun
Nalan
N
Demirayak
Seref
S
Güven
Klymet
K
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007259:Infrared Rays; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008795:Metronidazole / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D009593:Nitroimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D009593:Nitroimidazoles; D008795:Metronidazole