89-24-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Phenylhydantoin is used as an active pharmaceutical ingredient for the development of antiepileptic drugs. Its ability to bind to voltage-dependent sodium channels (NVSC) makes it a potential candidate for the treatment of epilepsy and other seizure disorders.
Used in Research and Development:
5-Phenylhydantoin is used as a research compound to study the mechanisms of action of antiepileptic drugs and to develop new therapeutic agents with improved efficacy and safety profiles. Its role in binding to voltage-dependent sodium channels (NVSC) provides valuable insights into the development of novel anticonvulsant medications.
Used in Metabolism Studies:
As a metabolite of Mephenytoin, 5-Phenylhydantoin is used in metabolism studies to understand the metabolic pathways and enzyme activities involved in the breakdown and elimination of antiepileptic drugs. This information can help in optimizing drug dosages and minimizing side effects.
Used in Quality Control and Analysis:
5-Phenylhydantoin is used as a reference compound in the quality control and analysis of pharmaceutical products containing Mephenytoin or other related antiepileptic drugs. Its chemical properties and reactivity can be utilized to develop analytical methods for the accurate determination of drug concentrations in various matrices.

InChI:InChI=1/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)

Upstream product

• 88169-89-5 2-phenyl-2-ureidoacetonitrile 
• 538-51-2 benzylidene phenylamine 
• 100-52-7 benzaldehyde 
• 1074-12-0 phenylglyoxal hydrate 
• 57-13-6 urea 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 29574-75-2 2,2-dihydroxy-1,3-diphenylpropan-1,3-dione 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 16750-42-8 2-amino-2-phenylacetonitrile 
• 532-28-5 (RS)-mandelonitrile 
• 506-87-6 ammonium carbonate 
• 13603-49-1 α-hydroxy-α-methylthio-acetophenone 
• 151-50-8 potassium cyanide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 131732-36-0 (4-benzyl-2,5-dioxo-imidazolidin-1-yl)-acetic acid ethyl ester 
• 6794-69-0 4-phenyl-1,3-dihydro-imidazol-2-one 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 15900-38-6 5-hydroxy-5-phenyl-imidazolidine-2,4-dione 
• 62371-82-8 5,4'-diphenyl-dihydro-[1,4']biimidazolyl-2,4,2',5'-tetraone 
• 59760-95-1 bromo-5 phenyl-5 hydantoine 
• 150-30-1 Phenylalanine 
• 68319-44-8 4-<(4-nitrophenyl)methyl>imidazolidine-2,5-dione 
• 82264-50-4 N-carbamoyl-D,L-phenylglycine 
• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 
• 18749-95-6 4,4'-diphenyl-tetrahydro-[4,4']biimidazolyl-2,5,2',5'-tetraone 
• 6846-11-3 3-methyl-5-phenylimidazolidine-2,4-dione 
• 27129-49-3 4-phenylimidazolidin-2-one 
• 875-74-1 (R)-phenylglycine 

Relevant academic research and scientific papers

MACROMOLECULAR COMPOSITIONS FOR BINDING SMALL MOLECULES

The present invention relates to a method for preparing a macromolecular composition comprising phenylglyoxaldehyde-derivatives. The invention also relates to the macromolecular compositions per se, and to methods of using the macromolecular compositions. The macromolecular compositions are useful for undergoing subsequent reactions with small molecules, for instance to remove such small molecules from a solution.

Method for continuously and quickly preparing DL-phenylglycine and analogue thereof

The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.

Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates

A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.

HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R3c, R4a, R4b, R5, R6, Z and X are as defined herein are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins

Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).

Continuous Synthesis of Hydantoins: Intensifying the Bucherer-Bergs Reaction

A continuous Bucherer-Bergs hydantoin synthesis utilizing intensified conditions is reported. The methodology is characterized by a two-feed flow approach to independently feed the organic substrate and the aqueous reagent solution. The increased interfacial area of the biphasic reaction mixture and the lack of headspace enabled almost quantitative conversions within ca. 30 minutes at 120 °C and 20 bar even for unpolar starting materials. In addition, a selective N(3)-monoalkylation of the resulting heterocycles under batch microwave conditions is reported yielding potential acetylcholinesterase inhibitors.

A one-pot synthesis of 5,5-disubstituted hydantoin derivatives using magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst

A facile and rapid method for the one-pot synthesis of 5,5-disubstituted hydantoins in the presence of magnetic Fe3O4 nanoparticles has been developed. The multicomponent reactions of carbonyl compounds (aldehydes and ketones), potassium cyanide and ammonium carbonate were carried out under solvent-free conditions to obtain various hydantoin derivatives. The magnetic catalyst could be readily separated by an external magnet from the reaction mixture. This procedure has many advantages, such as the use of a reusable magnetic catalyst, high yields, short reaction times, simplicity and very easiness with implementing the methodology.

Microwave-promoted facile and rapid synthesis procedure for the efficient synthesis of 5,5-disubstituted hydantoins

A fast, general, environmentally friendly, and facile method for preparation of 5, 5-disubstituted hydantoins from the reaction between ketone (or aldehyde) derivatives with KCN and ammonium carbonate under microwave irradiation is presented. The microwaves remarkably accelerated this reaction, the reaction times decreased dramatically, the reaction conditions were milder, and the yields were also greater. Also a comparative study of microwave versus classical conditions has been done. All the products were characterized by infrared, NMR, and CHN analysis, and their melting points are identical to those of the known compounds reported in the literature. This method might be useful in the future for the preparation of similar derivatives. Taylor & Francis Group, LLC.

Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: Byproduct-free prenylation of hydantoins

The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2) 2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a-1f at the diene C4-position to furnish products of n-prenylation 2a-2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed.

Facile one-pot synthesis of 5-substituted hydantoins

5-Substituted and 5,5-disubstituted hydantoins are synthesised from the corresponding aldehydes or ketones, using a one-pot, gallium(iii) triflate-catalysed procedure that is compatible with a range of substrates and solvents.