Synthesis and antibacterial activity of triazole and isoxazole derivatives of ampicillin.
In order to improve the antibacterial activity of ampicillin, new penicillin derivatives having a 1-aryltriazole-4-carboxamide group or a 5-arylisoxazole-3-carboxamide group at the alpha-position of benzylpenicillin or p-hydroxybenzylpenicillin were synthesized. Some compounds in these series were found to possess high activity against Pseudomonas and other Gram-negative bacteria. In addition, structure-activity relationships, especially the effect of the hydrophobic character of the compounds on activity, were investigated.
D000667:Ampicillin / Q000138:chemical synthesis* / Q000633:toxicity; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D007202:Indicators and Reagents; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010080:Oxazoles / Q000138:chemical synthesis*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000633:toxicity
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007555:Isoxazoles; D010080:Oxazoles; D014230:Triazoles; D000667:Ampicillin