Synthesis and structure-activity studies of antibacterial oxazolidinones containing dihydrothiopyran or dihydrothiazine C-rings

Bioorganic & Medicinal Chemistry Letters
Adam R RensloMikhail F Gordeev

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.

References

Apr 8, 2003·Current Topics in Medicinal Chemistry·Douglas K Hutchinson

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Citations

Sep 5, 2008·Bioorganic & Medicinal Chemistry Letters·Mohamed TakhiJaved Iqbal
Feb 14, 2015·Chemical Biology & Drug Design·Yan ChenWei-Min Chen
Mar 11, 2006·Bioorganic & Medicinal Chemistry·Adam R RensloMikhail F Gordeev
Jan 1, 2012·International Journal of Medicinal Chemistry·Neha PanditBirendra Shrivastava
Dec 16, 2019·Bioorganic Chemistry·G D García-OlaizRafael Laniado-Laborín

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