Imidazolidinones structurally-related to penicillins: synthesis, molecular modeling and biological evaluation.
Several bicyclic imidazolidinones structurally-related to penicillins have been prepared from penam precursors. The compounds were compared to benzylpenicillin as active reference, using the methods of theoretical chemistry. Structures 7 and 8, in which the acyl group of the side-chain was anchored, via a "one-atom spacer", at position N-7 of the imidazolidinone ring, appeared as good penicillin mimics. However, they were found devoid of significant antibacterial activity.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D019295:Computational Biology; D015195:Drug Design; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D010400:Penicillin G / Q000494:pharmacology; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D007093:Imidazoles; D007202:Indicators and Reagents; D010406:Penicillins; D010400:Penicillin G