Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.
A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated.
Yan
Shanshan
S
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Miller
Marvin J
MJ
Wencewicz
Timothy A
TA
Möllmann
Ute
U
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000502:physiology; D008826:Microbial Sensitivity Tests; D009603:Nitroso Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D009603:Nitroso Compounds; D023303:Oxazolidinones