380380-56-3

Basic information

• Product Name: (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE
• Synonyms: (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE
• CAS NO: 380380-56-3
• Molecular Formula: C₁₀H₁₁FN₂O₂
• Molecular Weight: 210.2
• Mol File: 380380-56-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE(380380-56-3)
• EPA Substance Registry System: (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE(380380-56-3)

Safety Data

• Hazardous Substances Data: 380380-56-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE is used as an antibiotic for the treatment of various bacterial infections, particularly those caused by Gram-positive bacteria. Its application is due to its ability to inhibit bacterial protein synthesis, which prevents the bacteria from multiplying and spreading.
Used in Treatment of Skin and Soft Tissue Infections:
In the medical field, (S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE is used as an antibiotic for treating skin and soft tissue infections. Its effectiveness in this application is attributed to its potent action against Gram-positive bacteria, which are common causes of such infections.
Used in Treatment of Pneumonia:
(S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE is also used as an antibiotic for the treatment of pneumonia, especially when the infection is caused by Gram-positive bacteria. Its use in this context is due to its ability to effectively target and inhibit the growth of the bacteria responsible for the pneumonia.

Upstream product

• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 372-19-0 meta-fluoroaniline 
• 380380-55-2 [(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate 
• 149524-44-7 (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide 

Downstream Products

• 501940-28-9 (5R)-3-(3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one 
• 851379-37-8 C₂₇H₃₂FN₃O₇ 
• 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 
• 139071-79-7 (S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 851379-34-5 C₁₅H₁₇FN₂O₅ 

Relevant articles and documents

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.

BIFUNCTIONAL MACROLIDE HETEROCYCLIC COMPOUNDS AND MEHTODS OF MAKING AND USING THE SAME

The present invention relates generally to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to a family of bifunctional compounds useful as therapeutic agents. These com