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Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.

ABSTRACT: 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.

SUBMITTER: Yan S

PROVIDER: S-EPMC2818252 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.

Yan Shanshan S Miller Marvin J MJ Wencewicz Timothy A TA Möllmann Ute U

Bioorganic & medicinal chemistry letters 20091008 3

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. ...[more]

PMID: 20031407

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