PMID: 2118186Sep 1, 1990Paper

Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 2. The "A" group

Journal of Medicinal Chemistry
W A GregoryM A Wuonola

Abstract

The synthesis and structure-activity relationship (SAR) studies of the effect of varying the "A" group in a series of 5-(acetamidomethyl)oxazolidonone antibacterials (2) are described. Compounds 2 were principally prepared either by the six-step synthesis described previously (J. Med. Chem. 1989, 32, 1673) or by elaboration of the synthetic intermediate 2 (A = H) via electrophilic aromatic substitution or elaboration of the intermediate 2 (A = I) by transition metal catalyzed carbon-carbon bond-forming reactions. Antibacterial evaluation of compounds 2 with A = alkyl, ethenyl, ethynyl, hydroxyalkyl, aldo and keto, oximinoakyl, carboalkoxy, nitro, amino, halo and psi-halo, alkylthio, alkylsulfinyl, and alkysulfonyl against Staphylococcus aureus and Enterococcus faecalis led to the identification of several SAR trends. In several series of homologues (alkyl, ketyl, aximinoalkyl, amino, halo and psi-halo, and alkythio), antibacterial activity increased with increasing lipophilicity. But in series with where A is a substituent with a trior tetrasubstituted (substituent larger than H) quaternary atom attached directly to the aromatic ring (hydroxyalkyl, alkylsulfinyl, alkylsufonyl), the activity peaked at the member of the series wi...Continue Reading

Citations

Sep 1, 1992·Diagnostic Microbiology and Infectious Disease·W Brumfitt, J M Hamilton-Miller
Nov 19, 2003·Bioorganic & Medicinal Chemistry Letters·Michael B GravestockAlan Wookey
Apr 18, 2002·Bioorganic & Medicinal Chemistry Letters·Du Yu, Guo Huiyuan
Feb 3, 2007·Chemical & Pharmaceutical Bulletin·Sunil Kumar Reddy AaramadakaMagesh Vijayan
Dec 24, 2011·Annals of the New York Academy of Sciences·Karen Joy Shaw, Michael R Barbachyn
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