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Usage

Uses

Used in Pharmaceutical Research and Development:
(S)-N-[[3-(3-Fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide is utilized as a compound in pharmaceutical research and development for its potential biological activity or reactivity. Its complex structure makes it a candidate for drug discovery, where it may be further studied and modified to develop new therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-N-[[3-(3-Fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide is employed as a starting material or intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its unique structural features may contribute to the development of novel drugs with improved efficacy and selectivity.

InChI:InChI=1/C12H13FN2O3/c1-8(16)14-6-11-7-15(12(17)18-11)10-4-2-3-9(13)5-10/h2-5,11H,6-7H2,1H3,(H,14,16)/t11-/m0/s1

Upstream product

• 149524-44-7 (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide 
• 380380-56-3 (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 321430-28-8 3-fluorophenylcarbamic acid 2-methylpropyl ester 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 372-19-0 meta-fluoroaniline 
• 108-24-7 acetic anhydride 
• 380380-55-2 [(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate 
• 404-71-7 1-fluoro-3-isocyanatobenzene 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 

Downstream Products

• 232950-90-2 5-(S)-Acetamidomethyl-3-[4'-formyl-3'-fluorophenyl]oxazolidine-2-one 
• 1333991-97-1 C₂₃H₁₈F₂N₆O₃ 
• 1333992-00-9 C₂₂H₁₈FN₇O₃ 
• 1333992-01-0 C₂₃H₁₉FN₆O₃ 
• 1333992-03-2 C₂₄H₂₁FN₆O₄ 
• 1333992-05-4 C₂₁H₁₇FN₆O₃S 
• 149524-45-8 (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide 
• 165800-03-3 linezolid 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents. 2. Modification of the phenyl ring - The potentiating effect of fluorine substitution on in vivo activity

Various electron-withdrawing groups were incorporated into the meta position of tropone-substituted 3-phenyl-2-oxazolidinones and their influence on antibacterial activity examined. Consideration of in vitro and in vivo test results indicated that one or two fluorine atoms flanking the para tropone appendage is the optimum arrangement for these compounds. Synthetic routes to enantiomerically enriched analogues are reported. Copyright

Installation of an aryl boronic acid function into the external section of N-aryl-oxazolidinones: Synthesis and antimicrobial evaluation

N-aryl-oxazolidinones is a prominent family of antimicrobials used for treating infections caused by clinically prevalent Gram-positive bacteria. Recently, boron-containing compounds have displayed intriguing potential in the antibiotic discovery setting. Herein, we report the unprecedented introduction of a boron-containing moiety such as an aryl boronic acid in the external region of the oxazolidinone structure via a chemoselective acyl coupling reaction. As a result, we accessed a series of analogues with a distal aryl boronic pharmacophore on the oxazolidinone scaffold. We identified that a peripheric linear conformation coupled with freedom of rotation and no further substitution on the external aryl boronic ring, an amido linkage with hydrogen bonding character, in addition to a para-relative disposition between boronic group and linker, are the optimal combination of structural features in this series for antimicrobial activity. In comparison to linezolid, the analogue comprising all those features, compound 20b, displayed levels of antimicrobial activity augmented by an eight-fold to a thirty-two-fold against a panel of Gram-positive strains, and a near one hundred-fold against Escherichia coli JW5503, a Gram-negative mutant strain with a defective efflux capability.

Incorporation of a chiral gem-disubstituted nitrogen heterocycle yields an oxazolidinone antibiotic with reduced mitochondrial toxicity

gem-Disubstituted N-heterocycles are rarely found in drugs, despite their potential to improve the drug-like properties of small molecule pharmaceuticals. Linezolid, a morpholine heterocycle-containing oxazolidinone antibiotic, exhibits significant side effects associated with human mitochondrial protein synthesis inhibition. We synthesized a gem-disubstituted linezolid analogue that when compared to linezolid, maintains comparable (albeit slightly diminished) activity against bacteria, comparable in vitro physicochemical properties, and a decrease in undesired mitochondrial protein synthesis (MPS) inhibition. This research contributes to the structure-activity-relationship data surrounding oxazolidinone MPS inhibition, and may inspire investigations into the utility of gem-disubstituted N-heterocycles in medicinal chemistry.

Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents. Part II

The synthesis and antibacterial activity of 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinones is reported. Compound 3e with a 2,4-disubstituted thiophene ring was found to be a potent inhibitor of Gram-positive pathogens and was 4-16-fold more potent than Linezolid.

The synthesis of N-aryl-5(S)-aminomethyl-2-oxazolidinone antibacterials and derivatives in one step from aryl carbamates

Since 1993, a significant process research and development effort directed towards the large-scale synthesis of oxazolidinone antibacterial agents has been ongoing in both Early Chemical Process Research and Development, and Chemical Process Research and Development at Pharmacia. This work has led to the successful development of the current commercial process to produce Zyvox (linezolid), recently approved by the FDA as an antibacterial. While this synthesis is appropriate for the preparation of linezolid in particular, a more convergent and versatile synthesis was developed for the rapid preparation of numerous other oxazolidinone analogues. Toward this end, economical methods for the large-scale preparation of N-[(2S)-2-(acetyloxy)-3-chloropropyl]acetamide 3 and tert-butyl [(2S)-3-chloro-2-hydroxypropyl]carbamate 27 from commercially available (S)-epichlorohydrin via the common intermediate (2S)-1-amino-3-chloro-2-propanol hydrochloride 2a were developed. Also, general methods for coupling these reagents with N-aryl carbamates to give N-aryl-5(S)-aminomethyl-2-oxazolidinone derivatives in one step were developed. These reagents and procedures have proven widely applicable in the preparation of a diverse array of oxazolidinone analogues such as 23 and 28 in both process and medicinal chemistry research.

Novel oxazolidinone derivatives and a process for the preparation thereof

The present invention relates to novel oxazolidinone derivatives, their pharmaceutically acceptable salts and a process for the preparation thereof. More particularly, the present invention relates to oxazolidinone derivatives having pyridine or pyrimidine moeity substituted by heterocycle and heteroaromaticcycle at 4-position of phenyl ring. The compounds of the present invention have wide antibacterial spectrum, superior antibacterial activity and low toxicity, such that the compound of this invention can be used as an antibacterial agent.

Process to prepare oxazolidinones

The present invention relates to a one-step process to prepare pharmacologically active 2-oxo-5-oxazolidinylmethylacetamides.

Substituted aryl- and heteroaryl-phenyloxazolidinones

The present invention discloses novel substituted aryl- and heteroarylphenyloxazolidinones which are useful as anti-bacterial agents. More specifically, the substituted aryl- and heteroarylphenyloxazolidinones of the invention are characterized by oxazoli