title: Synthesis and structure-activity studies of antibacterial oxazolidinones containing dihydrothiopyran or dihydrothiazine C-rings.
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.
authors.affiliation: Pfizer Global Research and Development, 34790 Ardentech Ct. Fremont, CA 94555, USA. adam.renslo@ucsf.edu
authors.forename: Adam R
authors.initials: AR
authors.lastname: Renslo
authors.forename: Gary W
authors.initials: GW
authors.lastname: Luehr
authors.forename: Stuart
authors.initials: S
authors.lastname: Lam
authors.forename: Neil E
authors.initials: NE
authors.lastname: Westlund
authors.forename: Marcela
authors.initials: M
authors.lastname: Gómez
authors.forename: Corrine J
authors.initials: CJ
authors.lastname: Hackbarth
authors.forename: Dinesh V
authors.initials: DV
authors.lastname: Patel
authors.forename: Mikhail F
authors.initials: MF
authors.lastname: Gordeev
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D023303:Oxazolidinones