2216-93-5

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Imidazolidinedione, 5-ethyl-5-phenyl-, (+-)is used as an anti-seizure medication for the treatment of epilepsy and certain types of seizures. It is utilized to stabilize electrical activity in the brain, helping to prevent seizures from occurring.
Used in Combination Therapy:
Phenytoin is used as a component in combination therapy with other medications to control seizures more effectively. This approach can be beneficial for patients whose seizures are not adequately managed by a single medication.

Upstream product

• 75356-44-4 (1-cyano-1-phenyl-propyl)-urea 
• 74-90-8 hydrogen cyanide 
• 124-38-9 carbon dioxide 
• 93-55-0 1-phenyl-propan-1-one 
• 298689-33-5 2-amino-2-phenylbutyronitrile 
• 33875-36-4 2-Isocyanato-2-phenyl-butyronitrile 
• 75356-44-4 (1-Cyano-1-phenyl-propyl)-urea 
• 506-87-6 ammonium carbonate 
• 75356-38-6 racem-α-Aethyl-α-cyan-benzylisocyanat 
• 75-44-5 phosgene 
• 102-09-0 bis(phenyl) carbonate 
• 5438-07-3 2-amino-2-phenylbutanoic acid 
• 57-13-6 urea 
• 80544-75-8 (rac)-2-Cyan-2-phenylbutanamid 

Downstream Products

• 50-12-4 mephenytoin 
• 65567-34-2 (+)-Nirvanol 
• 65567-32-0 (-)-Nirvanol 
• 5062-78-2 4-Ethyl-4-phenylimidazolidin-2-on 
• 21435-70-1 5-ethyl-5-phenyl-3-(toluene-4-sulfonyl)-imidazolidine-2,4-dione 
• 771515-54-9 C₁₉H₂₀N₂O₂ 
• 857037-18-4 C₁₈H₁₇ClN₂O₂ 
• 849190-27-8 C₁₈H₁₇BrN₂O₂ 
• 778619-05-9 4-[(4-ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)methyl]-benzonitrile 
• 790676-34-5 5-ethyl-3-(4-methoxybenzyl)-5-phenyl-2,4-imidazolidinedione 
• 93879-40-4 (+/-)-N-3-benzyl-Nirvanol 
• 51323-57-0 5-ethyl-3-(4-nitro-benzyl)-5-phenyl-imidazolidine-2,4-dione 
• 94107-58-1 2-amino-2-phenylbutanoic acid hydrochloride 
• 968-51-4 5-ethyl-3-morpholin-4-ylmethyl-5-phenyl-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

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.

Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins

Palladium(II) trifluoroacetate (5 mol %) catalyzes the C-arylation of N,N-disubstituted hydantoins by aryl iodides in good yield. The reaction proceeds through base-promoted enolization of the amino acid derived hydantoins, and the resulting 5,5-disubstituted hydantoins may be deprotected at one or both N atoms to yield biologically active structures or alternatively hydrolyzed to the parent α-aryl α-amino acids. The reaction is successful with a variety of parent amino acids and a range of electron-rich and electron-poor aryl iodides.

New derivatives of hydantoin as potential antiproliferative agents: Biological and structural characterization in combination with quantum chemical calculations

Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer

Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study

To obtain insight into the interactions of potential anticonvulsant drugs with their surrounding, two series of 5-methyl-5-aryl- and 5-ethyl-5- -arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of Kamlet and Taft. The ratio of the contributions of specific and non-specific solvent-solute interactions were correlated with the corresponding absorption, distribution, metabolism, and excretion (ADME) properties of the studied compounds. The correlation equations were combined with different physicochemical parameters to generate new equations, which demonstrate the reasonable relationships between the solvent- solute interactions and the structure-activity parameters. Copyright (C)2013 SCS.

Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents

Considering the importance of hydantoin derivatives in treatment of status epilepticus, four 5-phenylhydantoins, whose lipophilicities were estimated to be similar to that of phenytoin, were synthesized. Evaluation of their anticonvulsant activities was performed on rats by subcutaneous pentylenetetrazol seizure test and intravenous pentylenetetrazol threshold test, and spontaneous locomotor activity test was used to assess possible sedative effects. X-ray analysis of three compounds suggested that certain analogies might be drawn between interactions in crystal packing and biological interactions responsible for their anticonvulsant activity. It was found that 5-ethyl-5-phenyl- 3-propylhydantoin exhibits the most favorable pharmacological properties among the synthesized compounds, i.e., anticonvulsant activity comparable to phenytoin with lower liability for induction of sedation in rats.

Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins

A series of 5-substituted 5-phenylhydantoins was synthesized and their UV absorption spectra were recorded in the region 200-400 nm in selected solvents of different polarity. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen-bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The lipophilicities of the investigated hydantoins were estimated by calculation of their log P values. The quantitative relationship between the ratio of the contributions of specific solvent interactions and the corresponding lipophilicity parameter is discussed. The correlation equations were combined with the corresponding ED50 values and different physicochemical parameters to generate new equations that demonstrate the reasonable relationships between solute-solvent interactions and the structure-activity parameters. In order to determine a spectroscopic assignment of the absorption bands in different solvents, quantum chemical calculations were done. Springer-Verlag 2011.

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.

Racemic and Optically Active Hydantoins from Disubstituted Cyanoacetic Acids

Starting from the chiral disubstituted cyanoacetic acids 1 the racemates and some enantiomers of the 5,5-disubstituted hydantoins 6 and of the 3-methylhydantoins 7 are synthesized via the isocyanates 3.Their absolute configurations are determined.

Acetohydroxamic acids

The invention provides new acetohydroxamic acid derivatives, having interesting properties on the central nervous system, of the formula: R1 R2 R3 C-CO-NHOH, in which R2 and R3 are each hydrogen or C1-6 alkyl, and R1 is C1-6 alkyl Z1 Z2 N (where Z1 and Z2 are each phenyl, substituted phenyl, or cycloalkyl), substituted hydantoinyl, benzhydroxylcarboxamido, Z3 CH2 -- (where Z3 = optionally substituted aryl), Z4 -A- (where Z4 is optionally substituted phenyl or naphthyl, and A is --NH--, --N(C1-4 alkyl)--, --N(C5-6 cycloalkyl)--, --NHCO--, --N(C1-4 alkyl)CO--, --N(C5-6 cycloalkyl)CO--, --CONH--, --CON(C1-4 alkyl)--, --CON(C5-6 cycloalkyl)--, --NHCONH--, --N(C5 H6)CONH--, or --N(substituted phenyl)CONH--, optionally substituted benzimidazolyl, or an optionally substituted tricyclic radical, and their metal and acid addition salts.