title: Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The "B" group.
abstract: The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.
authors.affiliation: Medical Products Department, E. I. du Pont de Nemours and Co., Wilmington, Delaware 19898.
authors.forename: W A
authors.initials: WA
authors.lastname: Gregory
authors.forename: D R
authors.initials: DR
authors.lastname: Brittelli
authors.forename: C L
authors.initials: CL
authors.lastname: Wang
authors.forename: M A
authors.initials: MA
authors.lastname: Wuonola
authors.forename: R J
authors.initials: RJ
authors.lastname: McRipley
authors.forename: D C
authors.initials: DC
authors.lastname: Eustice
authors.forename: V S
authors.initials: VS
authors.lastname: Eberly
authors.forename: P T
authors.initials: PT
authors.lastname: Bartholomew
authors.forename: A M
authors.initials: AM
authors.lastname: Slee
authors.forename: M
authors.initials: M
authors.lastname: Forbes
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D013293:Enterococcus faecalis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D010080:Oxazoles