112459-79-7

Usage

Uses

Used in Biomedical Research:
N-BUTYRYL-4-(S)-PHENYLMETHYL-2-OXAZOLIDINONE is used as a negative control for the Cell Sheet Migration Inhibitor in biomedical research. It serves as a reference point to compare the effects of other compounds on cell migration, allowing researchers to better understand the mechanisms and factors involved in this process.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-BUTYRYL-4-(S)-PHENYLMETHYL-2-OXAZOLIDINONE may be used as a starting point for the development of new drugs targeting cell migration-related diseases. Its properties as a negative control can help researchers identify potential therapeutic agents that can modulate cell migration effectively.
Used in Drug Delivery Systems:
Similar to gallotannin, N-BUTYRYL-4-(S)-PHENYLMETHYL-2-OXAZOLIDINONE could potentially be incorporated into drug delivery systems to improve the bioavailability and therapeutic outcomes of various pharmaceutical agents. Its oil-like chemical properties may facilitate its incorporation into different types of carriers, such as organic and metallic nanoparticles.

Upstream product

• 62763-37-5 butyric O-ethyl-carbonic anhydride 
• 101711-90-4 (S)-4-benzyl-2-oxazolidinone lithium salt 
• 2314-97-8 iodotrifluoromethane 
• 90719-30-5 (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 673-06-3 D-(R)-phenylalanine 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 107-92-6 butyric acid 
• 141-75-3 butyryl chloride 
• 143097-09-0 (R)-4-benzyl-3-(trimethylsilyl)-2-oxazolidinone 
• 106-31-0 butanoic acid anhydride 

Downstream Products

• 130710-56-4 (S)-3-<(R)-2-ethyl-1-oxo-4-penten-1-yl>-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 156546-60-0 (S)-4-Benzyl-3-((S)-2-phenylsulfanyl-butyryl)-oxazolidin-2-one 
• 163457-34-9 (+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone 
• 500220-39-3 (S)-4-Benzyl-3-[(E)-(2S,3R,5R,6R,7R,8S)-5-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-3-hydroxy-7-methoxy-6,8-dimethyl-dodec-10-enoyl]-oxazolidin-2-one 
• 209671-27-2 (4S)-3-((2'S,3'R)-2'-ethyl-3'-hydroxy-4'-methylpentanoyl)-4-phenylmethyl-2-oxazolidinone 
• 215177-83-6 (4S,2'S,3'R)-3-(2'-ethyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone 
• 371115-19-4 4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone 
• 852207-75-1 (S)-4-Benzyl-3-((2S,3R)-5-benzyloxy-2-ethyl-3-hydroxy-pentanoyl)-oxazolidin-2-one 
• 157405-12-4 (+)-(4S)-3-<(2'R)-2'-((tert-Butyldimethylsiloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone 
• 1009089-91-1 (4S)-4-benzyl-3-((2R,3S,4R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-2-ethyl-3-hydroxy-4-methylpentanoyl)-1,3-oxazolan-2-one 
• 1035609-60-9 C₂₃H₂₅NO₅ 
• 1138452-96-6 C₄₂H₅₇NO₇Si 
• 150615-45-5 (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone 
• 1178869-84-5 C₂₃H₂₇NO₅ 

Relevant academic research and scientific papers

Combined Cardioprotective and Adipocyte Browning Effects Promoted by the Eutomer of Dual sEH/PPARγModulator

The metabolic syndrome (MetS) is a constellation of cardiovascular and metabolic symptoms involving insulin resistance, steatohepatitis, obesity, hypertension, and heart disease, and patients suffering from MetS often require polypharmaceutical treatment.

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.

Synthesis of (+)-Tacamonine via Stereoselective Radical Cyclization

A concise, asymmetric synthesis of the indole alkaloid (+)-tacamonine is reported involving a stereoselective radical cyclization of a 1-phenylsulfanyl tetrahydro-β-carboline bearing a pendant enoate ester side chain as a key step. In this process, a sing

Asymmetric total synthesis of four stereoisomers of the sex pheromone of the western corn rootworm

A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.

Synthesis method and application of diabrotica virgifera virgifera le conte sex pheromone

The invention belongs to the technical field of pesticide chemistry, and discloses a synthesis method and application of diabrotica virgifera virgifera le conte sex pheromone. The synthesis method comprises the steps of enabling chiral sulfone compounds, i.e., (S)-2-methylbutyl thiazolsulfone and (R)-2-methylbutyl thiazolsulfone to be respectively subjected to a Julia-Kocienski coupling reaction with chiral aldehyde compounds, i.e., (S)-6-aldehyde hexan-2-ol propionate and (R)-6-aldehyde hexan-2-ol propionate, and carrying out hydrogenation reduction on the product of the coupling reaction soas to obtain the diabrotica virgifera virgifera le conte sex pheromone. In addition, the diabrotica virgifera virgifera le conte sex pheromone prepared by the method can be applied to the prevention and control of diabrotica virgifera virgifera le conte. The synthetic route of the diabrotica virgifera virgifera le conte sex pheromone is simplified, fewer by-products are produced in the reaction, and the reaction yield is greatly increased.

Stereoselective synthesis of the Paulownia bagworm sex pheromone

According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.

A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose

Aggrecanase-1 and -2 (ADAMTS-4 and ADAMTS-5) are zinc metalloproteases involved in the degradation of aggrecan in cartilage. Inhibitors could provide a means of altering the progression of osteoarthritis. We report the identification of 7 which had good oral pharmacokinetics in rats and showed efficacy in a rat chemical model of osteoarthritis. The projected human dose required to achieve sustained plasma levels ≥10 times the hADAMTS-5 IC50 is 5 mg q.d.

Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization

Polyketide synthases (PKSs) represent a powerful catalytic platform capable of effecting multiple carbon-carbon bond forming reactions and oxidation state adjustments. We explored the functionality of two terminal PKS modules that produce the 16-membered tylosin macrocycle, using them as biocatalysts in the chemoenzymatic synthesis of tylactone and its subsequent elaboration to complete the first total synthesis of the juvenimicin, M-4365, and rosamicin classes of macrolide antibiotics via late-stage diversification. Synthetic chemistry was employed to generate the tylactone hexaketide chain elongation intermediate that was accepted by the juvenimicin (Juv) ketosynthase of the penultimate JuvEIV PKS module. The hexaketide is processed through two complete modules (JuvEIV and JuvEV) in vitro, which catalyze elongation and functionalization of two ketide units followed by cyclization of the resulting octaketide into tylactone. After macrolactonization, a combination of in vivo glycosylation, selective in vitro cytochrome P450-mediated oxidation, and chemical oxidation was used to complete the scalable construction of a series of macrolide natural products in as few as 15 linear steps (21 total) with an overall yield of 4.6%.

Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands

A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S2′ pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P2′ substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.