Eperezolid - CAS 165800-04-4
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Not Intended for Therapeutic Use. For research use only.
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Eperezolid(PNU-100592) is a oxazolidinone antibacterial agent, Eperezolid demonstrated good in vitro inhibitory activity, regardless of methicillin susceptibility for staphylococci(MIC90= 1-4 mg/ml).
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PNU-100592; PNU100592; PNU 100592
1.Synthesis of eperezolid-like molecules and evaluation of their antimicrobial activities.
Yolal M1, Basoglu S, Bektas H, Demirci S, Alpay-Karaoglu S, Demirbas A. Bioorg Khim. 2012 Sep-Oct;38(5):610-20.
3-Fluoro-4-(4-phenylpiperazin-1-yl)aniline (II) prepared from 3,4-difluoro nitrobenzene was converted to the corresponding Schiff bases (III) and (IV) by treatment with 4-methoxybenzaldehyde and indol-3-carbaldehyde, respectively. Treatment of amine (II) with 4-fluorophenyl isothiocyanate affordedthe corresponding thiourea derivative (V). Compound (V) was converted to thiazolidinone and thiazoline derivatives (VI) and (VII) by cyclocondensation with ethylbromoacetate or 4-chlorophenacylbromide, respectively. The synthesis of carbothioamide derivative (X) was performed starting from compound (II) by three steps. Treatment of compound (X) with sodium hydroxide, sulfuric acid, or chlorophenacyl bromide generated the corresponding 1,2,4-triazole (XI), 1,3,4-thiadiazole (XII), and 1,3-thiazolidinone (XIII) derivatives, respectively. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, 1H-NMR, 13C-NMR, and LC-MS) data.
2.Synthesis and antibacterial activities of eperezolid analogs with glycinyl substitutions.
Wang XJ1, Wu N, Du GJ, Zhao SQ, Yan M, Gu LQ. Arch Pharm (Weinheim). 2009 Jul;342(7):377-85. doi: 10.1002/ardp.200800233.
A series of eperezolid analogs with glycinyl substitutions were prepared and their antibacterial activities were studied against a panel of susceptible and resistant Gram-positive bacteria. The compounds with N-arylacyl or N-heteroarylacyl glycinyl structural units showed good antibacterial activities. The compounds 11b, 11c, and 11e were twofold more active than linezolid against Staphylococcus epidermidis and Enterococcus faecalis. Several pyridine analogs were also prepared and found to have poor antibacterial activity against most of the tested Gram-positive bacteria, however, one of the compounds 12e showed very high activity against Enterococcus faecalis.
3.In vitro activity of linezolid and eperezolid, two novel oxazolidinone antimicrobial agents, against anaerobic bacteria.
Yagi BH1, Zurenko GE. Anaerobe. 1997 Oct;3(5):301-6.
Linezolid (formerly U-100766) and eperezolid (formerly U-100592) are novel oxazolidinone antimicrobial agents that are active against multi-drug-resistant staphylococci, streptococci, enterococci, corynebacteria, and mycobacteria. Preliminary studies also demonstrated that the compounds inhibited some test strains of anaerobic bacteria. Therefore, we extended the in vitro evaluation of these agents to include a total of 54 different anaerobic species. Minimal inhibitory concentration (MIC) values were determined using a standard agar dilution method for 143 anaerobic bacterial isolates. Eperezolid and linezolid demonstrated potent activity against the anaerobic Gram-positive organisms with most MIC values in the range of 0.25-4 microg/mL. Viridans streptococci demonstrated MICs of 1-2 microg/mL; Peptostreptococcus species and Propionibacterium species were inhibited by </=0.25-1 microg/mL. Clostridial species were generally susceptible to the oxazolidinones (MICs of </=0.
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CAS 165800-04-4 Eperezolid

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