Antibacterial organophosphorus compounds: phosphoranilidohydrazones of 5-nitro-2-furaldehyde.
A series of phosphoranilidohydrazones of 5-nitro-2-furaldehyde was synthesized and evaluated for antibacterial activity. The series was prepared to examine the applicability of phosphoramidic hydrazones as carriers for the antibacterial nitrofuran moiety. Designed as analogues of nitrofurantoin, members of the series were chosen according to the Topliss approach to analogue design. The title compounds were devoid of gram-negative activity but possessed moderate antistaphylococcal activity. The most potent members of the series were equipotent with nitrofurantoin against Staphylococcus aureus. The relationship between structure and antistaphylococcal activity is discussed.
Jones
G S
GS
Department of Pharmaceutical Sciences, Bouve College of Pharmacy and Health Sciences, Northeastern University, Boston, MA 02115.
Daly
J S
JS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects; D005662:Furaldehyde / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009582:Nitrofurantoin / Q000031:analogs & derivatives; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006835:Hydrazones; D009943:Organophosphorus Compounds; D009582:Nitrofurantoin; D005662:Furaldehyde