TY - JOUR
T1 - Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry
AU - Yan, Shanshan
AU - Miller, Marvin J.
AU - Wencewicz, Timothy A.
AU - Möllmann, Ute
N1 - Funding Information:
We gratefully acknowledge the NIH ( GM 075855 ) for support of this research. We thank Uta Wohlfeld (HKI) for performing antibacterial assays. We also thank the Lizzadro Magnetic Resonance Research Center at Notre Dame for NMR facility and Nonka Sevova for mass spectroscopic analyses. TAW acknowledges the University of Notre Dame Chemistry–Biochemistry–Biology Interface (CBBI) Program and NIH Training Grant T32GM075762 for a fellowship.
PY - 2010/2/1
Y1 - 2010/2/1
N2 - 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.
AB - 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.
KW - Nitroso cycloaddition
KW - Oxazolidinone antibiotic analogs
UR - http://www.scopus.com/inward/record.url?scp=74049092281&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2009.10.018
DO - 10.1016/j.bmcl.2009.10.018
M3 - Article
C2 - 20031407
AN - SCOPUS:74049092281
SN - 0960-894X
VL - 20
SP - 1302
EP - 1305
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 3
ER -