(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one
[CAS# 189028-95-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one
• Synonyms: (4S)-4-Phenyl-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3-oxazolidin-2-one
• Molecular Formula: C₂₀H₂₀FNO₄
• Molecular Weight: 357.38
• CAS Registry Number: 189028-95-3
• EC Number: 606-165-0
• SMILES: C1[C@@H](N(C(=O)O1)C(=O)CCC[C@@H](C2=CC=C(C=C2)F)O)C3=CC=CC=C3

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 572.7±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 300.2±30.1 °C (Calc.)^*
• Index of refraction: 1.588 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one is a chemical compound that belongs to the class of oxazolidinone derivatives. These types of compounds have been investigated in various fields, particularly in medicinal chemistry, for their potential applications as antibacterial and anti-inflammatory agents.

The structure of this compound consists of a core oxazolidinone ring, which is substituted with a phenyl group and a hydroxy-pentanoyl group at specific positions. The compound also features a fluorophenyl group, which adds to its molecular complexity and may influence its pharmacological properties. The stereochemical configuration at the 4- and 5-positions of the oxazolidine ring is specified as (4S) and (5S), respectively, which indicates that these centers are configured in a specific three-dimensional arrangement that could impact the compound's biological activity.

The presence of a fluorophenyl group on the molecule suggests that it may have potential interactions with biological targets through its aromatic and electron-withdrawing fluorine substituent, which could modulate its activity in a variety of biological systems. The hydroxy-pentanoyl moiety might also contribute to the compound's potential in modulating enzymatic or receptor-based activities in the body.

While there may not be extensive data available on the specific applications of this compound, compounds with similar structures (oxazolidinones with aromatic substituents) have been explored as antimicrobial agents, particularly against Gram-positive bacteria. Oxazolidinones, as a class, are known for their mechanism of inhibiting bacterial protein synthesis by binding to the bacterial ribosome, and they have been used in the treatment of infections caused by resistant strains of bacteria.

Additionally, compounds with hydroxyl and phenyl groups are often studied for their potential to interact with biological targets involved in inflammatory responses, enzyme inhibition, or receptor modulation. Therefore, this compound could potentially have applications in medicinal chemistry for conditions requiring antibacterial or anti-inflammatory treatment.

As with any such compound, its full biological profile, including its efficacy, safety, and pharmacokinetic properties, would require further investigation through preclinical and clinical studies to better understand its potential therapeutic applications.

References

2009. Burkholderia cenocepacia: a new biocatalyst for efficient bioreduction of ezetimibe intermediate. Journal of Industrial Microbiology & Biotechnology, 36(10).
DOI: 10.1007/s10295-009-0622-z

2023. Ketoreductase-assisted synthesis of chiral selective tert-butyl{5-[(4-cyanophenyl)(hydroxy)methyl]-2-fluorophenyl}carbamate: process minutiae, optimization and characterization. Chemical Papers, 77(5).
DOI: 10.1007/s11696-023-02698-3