Synthesis and structure-activity studies of antibacterial oxazolidinones containing dihydrothiopyran or dihydrothiazine C-rings |
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Authors: | Renslo Adam R Luehr Gary W Lam Stuart Westlund Neil E Gómez Marcela Hackbarth Corrine J Patel Dinesh V Gordeev Mikhail F |
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Affiliation: | Pfizer Global Research and Development, 34790 Ardentech Ct. Fremont, CA 94555, USA. adam.renslo@ucsf.edu |
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Abstract: | A new series of antimicrobial oxazolidinones bearing unsaturated heterocyclic C-rings is described. Dihydrothiopyran derivatives were prepared from the saturated tetrahydrothiopyran sulfoxides via a Pummerer-rearrangement/elimination sequence. Two new synthetic approaches to the dihydrothiazine ring system were explored, the first involving a novel trifluoroacetylative-detrifluoroacetylative Pummerer-type reaction sequence and the second involving direct dehydrogenation of tetrahydrothiopyran S,S-dioxide intermediates. Final analogs such as 4 and 13 represent oxidized congeners of recent pre-clinical and clinical oxazolidinones. |
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