174649-04-8

Basic information

• Product Name: (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol
• Synonyms: (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol
• CAS NO: 174649-04-8
• Molecular Weight: 429.448
• Mol File: 174649-04-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol(174649-04-8)
• EPA Substance Registry System: (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol(174649-04-8)

Safety Data

• Hazardous Substances Data: 174649-04-8(Hazardous Substances Data)

Upstream product

• 903594-00-3 N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-(N-carbobenzoxypiperazinyl)aniline 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 212694-67-2 3-fluoro-4-(piperazin-1-yl)benzenamine 
• 239438-37-0 4-(4-amino-2-fluoro-phenyl)-piperazine-1-carboxylic acid benzyl ester 
• 174649-08-2 N-((S)-3-{4-[4-(2-Benzyloxy-acetyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 174649-06-0 (S)-N-[[3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 165800-04-4 eperezolid 
• 154590-66-6 (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 912552-57-9 4-{4-[benzyloxycarbonyl-(3-hydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 912552-58-0 4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 912552-59-1 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 60456-26-0 (R)-glycidyl butyrate 
• 174649-03-7 N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline 
• 1281885-22-0 3-fluoro-4-piperazin-1-yl-phenylamine dihydrochloride 

Downstream Products

• 903594-02-5 4-[2-Fluoro-4-((R)-5-methanesulfonyloxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperazine-1-carboxylic acid benzyl ester 
• 198410-25-2 (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 
• 239438-48-3 (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl azide 
• 1281885-30-0 (R)-benzyl 4-(2-fluoro-4-(2-oxo-5-(tosyloxymethyl)oxazolidin-3-yl)phenyl)piperazine-1-carboxylate 
• 154590-66-6 (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 1282094-22-7 (S)-N-((3-(3-fluoro-4-(4-(3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yloxy)propyl)piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide hydrochloride 
• 1622399-51-2 (S)-N-((3-(4-(4-(3-azidopropyl)piperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 1622399-52-3 (S)-N-((3-(3-fluoro-4-(4-(3-(4-phenyl-1H-1,2,3-triazol-1-yl)propyl)piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 1622399-53-4 (S)-N-((3-(3-fluoro-4-(4-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)piper-azin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 1622399-54-5 (S)-N-((1-(3-(4-(4-(5-(acetamidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazin-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetamide 
• 1622399-55-6 (S)-N-((3-(3-fluoro-4-(4-(3-(4-(((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)propyl)piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 216869-31-7 (R)-N-[[3-[3-fluoro-4-(N-piperazinyl)]-phenyl]-2-oxo-5-oxazolidinyl]methylalcohol 
• 174649-08-2 N-((S)-3-{4-[4-(2-Benzyloxy-acetyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 165800-04-4 eperezolid 

Relevant articles and documents

An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants

An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy.

Discovery of a novel nitroimidazolyl-oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation

A number of linezolid analogues containing a nitroaryl-1,3,4-thiadiazole moiety, were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analogue 1b exhibited more potent inhibitory activity, with respect to other synthesized compounds and reference drug linezolid. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that compound 1c exhibit potent antibacterial activity against Gram-positive bacteria at non-cytotoxic concentrations.

Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation

An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using d-proline-catalyzed asymmetric α-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis.