(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide
[CAS# 168828-89-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide
• Synonyms: 2-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione
• Molecular Formula: C₂₂H₂₀FN₃O₅
• Molecular Weight: 425.41
• CAS Registry Number: 168828-89-5
• SMILES: C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3=O)CN4C(=O)C5=CC=CC=C5C4=O)F

Properties

• Density: 1.44

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H319-H372-H410
• Precautionary Statements: P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330

Discovory and Applicatios

(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide is a chemically complex compound that falls within the class of oxazolidinones. This substance is notable for its potential application in antimicrobial therapy, owing to its structure, which is designed to maximize efficacy against resistant bacterial strains.

The discovery of this compound represents an effort to enhance the pharmacological profile of oxazolidinones, a class of antibiotics known for their ability to inhibit bacterial protein synthesis. Oxazolidinones, such as linezolid, have been used successfully to treat infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE). The design of (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide builds upon this framework by incorporating additional functional groups intended to enhance its antimicrobial activity and stability.

The compound features a phthalimide group attached to an oxazolidinone ring, which is crucial for its biological activity. The oxazolidinone ring is known for its ability to bind to the bacterial ribosome, thereby inhibiting protein synthesis. The presence of a phthalimide moiety, which is a five-membered ring containing two carbonyl groups, may influence the compound’s binding affinity and metabolic stability. This addition is expected to enhance the molecule’s overall efficacy and potentially its spectrum of activity.

The fluorine and morpholine substitutions on the phenyl ring are significant for their roles in improving the molecule's pharmacokinetic properties. Fluorine atoms are commonly used in drug design to increase metabolic stability and binding affinity. The morpholine group, known for its solubility-enhancing properties, helps the compound to penetrate biological membranes more effectively, improving its bioavailability.

The oxazolidinone ring's configuration, denoted by the (S)-prefix, indicates the compound’s stereochemistry, which is vital for its interaction with the bacterial ribosome. The stereochemistry of oxazolidinones plays a crucial role in determining their antimicrobial activity, as even minor changes can affect the molecule’s ability to bind to its target.

Applications of (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide are primarily focused on its potential as an antibiotic. The enhancements in the molecule’s structure suggest that it could be effective against a range of bacterial pathogens, particularly those resistant to existing treatments. Its development is part of a broader effort to address the challenge of antibiotic resistance by designing novel compounds with improved properties.

In addition to its antimicrobial applications, the compound could serve as a valuable tool in the pharmaceutical industry for further drug development. The oxazolidinone framework is versatile and can be modified to create new drugs targeting different biological processes, making it a promising candidate for research beyond antibiotics.