Recent development of potent analogues of oxazolidinone antibacterial agents

Expedient synthesis of an atypical oxazolidinone compound library

“…The Du Bois method was initially attempted with a number of appropriate carbamates (5), which were subjected to typical literature conditions for the C-H insertion reaction. 10 Unfortunately, the cyclised products 4 were not observed in appreciable quantities (Scheme 2).…”

“…t, J = 6.2 and 3. 5 Hz, H-7), 4.07 (1H, app. dd, J = 12.6 and 6.2 Hz, H-2), 3.31-3.38 (3H, m, H-6 and CHHCH3, under water peak, observed by COSY), 3.13-2.98 (3H, 3.13-2.98, m, H-4 and CHHCH3), 2.21-2.13 (1H, m, H-4), 1.78-1.70 (1H, m, H-3), 1.12 (3H, t, J = 7.2 Hz, CH3); 13 C NMR (101 MHz, DMSO-d6) δ 156.8…”

“…A) is the archetypal oxazolidonone antibiotic used for the treatment of Grampositive strains of methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE). 5 Antibacterial activity in this series usually requires substitution at the 5-position of the oxazolidinone ring with predictable stereochemistry, as exemplified by the most well developed analogue of 1, tedizolid (2, Figure 1. A) which displays activity in linezolid-resistant bacteria and was approved, as a phosphate prodrug, in 2014 in the USA to treat acute bacterial skin infections.…”

Synthesis and <i>in Vitro</i> Evaluation of the Antitubercular and Antibacterial Activity of Novel Oxazolidinones Bearing Octahydrocyclopenta[<i>c</i>]pyrrol-2-yl Moieties

“…5,[18][19][20] Among them, posizolid, 21) torezolid phosphate, 22) radezolid 23) and ranbezolid, 24) as shown in Fig. 1, are under development for the clinical treatment of tuberculosis and serious Gram-positive bacterial skin infections.…”

Potent Oxazolidinone Antibacterials with Heteroaromatic C-Ring Substructure

“…Oxazolidinone antibacterials are a class of synthetic antibiotics that have been developed over the last three decades 4,5 and are composed of an A-ring (oxazolidinone), B-ring (phenyl), and C-ring (an appropriate heterocycle, such as morpholine or piperazine), with a C-5 side chain unit on the A-ring substructure. Linezolid (1) was the first oxazolidinone antibiotic to be approved by the US Food and Drug Administration (FDA) and has been used for the treatment of serious infections caused by Gram-positive strains such as MRSA and VRE since 2000 ( Figure 1).…”