174649-05-9

Basic information

• Product Name: (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide
• Synonyms: (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide
• CAS NO: 174649-05-9
• Molecular Weight: 558.566
• Mol File: 174649-05-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide(174649-05-9)
• EPA Substance Registry System: (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide(174649-05-9)

Safety Data

• Hazardous Substances Data: 174649-05-9(Hazardous Substances Data)

Upstream product

• 1281885-30-0 (R)-benzyl 4-(2-fluoro-4-(2-oxo-5-(tosyloxymethyl)oxazolidin-3-yl)phenyl)piperazine-1-carboxylate 
• 1074-82-4 potassium phtalimide 
• 369-34-6 3,4-difluoronitrobenzene 
• 154590-33-7 1-(2-fluoro-4-nitrophenyl)piperazine 
• 903594-02-5 4-[2-Fluoro-4-((R)-5-methanesulfonyloxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperazine-1-carboxylic acid benzyl ester 

Downstream Products

• 154590-66-6 (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 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 
• 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 
• 198410-25-2 (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 

Relevant articles and documents

Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.

Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones.

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.