6617-78-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-Methoxyphenyl)hydantoin is used as an anticonvulsant medication for the treatment of certain types of seizures, specifically absence seizures. It is effective due to its ability to suppress abnormal electrical activity in the brain, providing relief to patients suffering from these conditions.
Used in Medical Treatment:
5-(4-Methoxyphenyl)hydantoin is used as a therapeutic agent for seizure management, particularly in cases where other anticonvulsant medications may not be effective or suitable. It is administered in tablet form and requires careful monitoring by healthcare providers to ensure optimal dosage and minimize side effects.

InChI:InChI=1/C10H10N2O3/c1-15-7-4-2-6(3-5-7)8-9(13)12-10(14)11-8/h2-5,8H,1H3,(H2,11,12,13,14)

Upstream product

• 872820-60-5 ethoxycarbonylamino-(4-methoxy-phenyl)-acetic acid amide 
• 151-50-8 potassium cyanide 
• 506-87-6 ammonium carbonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 143-33-9 sodium cyanide 
• 590-28-3 potassium cyanate 
• 79-11-8 chloroacetic acid 
• 119-52-8 4,4'-dimethoxybenzoin 
• 173904-10-4 5-bromohydantoin 
• 100-66-3 methoxybenzene 
• 42456-26-8 2-amino-2-(4-methoxyphenyl)acetonitrile 
• 124-38-9 carbon dioxide 
• 2393-23-9 4-methoxy-benzylamine 
• 52287-67-9 N-[(4-methoxyphenyl)(tosyl)methyl]urea 

Downstream Products

• 64952-07-4 5-cyclohexyl-hydantoin 
• 2540-53-6 2-(4-methoxyphenyl)glycine 
• 1443523-50-9 5-(4-methoxyphenyl)-5-(3-methylbut-2-enyl)-3-phenylmethyl-2,4-imidazolidinedione 
• 1443523-44-1 3-benzyl-5-(4-methoxyphenyl)hydantoin 
• 1015231-54-5 C₂₆H₁₄F₆N₄O₃ 
• 60781-72-8 DL-α-Benzyloxycarbonylamino-(4-methoxy-phenyl)-essigsaeure 
• 170119-36-5 Methoxycarbonylamino-(4-methoxy-phenyl)-acetic acid 

Relevant academic research and scientific papers

Different pathways in the reaction of N-(tosylmethyl)-substituted ureas, thioureas, and N′-cyanoguanidines with sodium cyanide. Synthesis of α-ureido nitriles, α-ureido amides, and hydantoin imino derivatives

Reaction of N-(tosylmethyl)-substituted ureas, thioureas, and N′-cyanoguanidines, prepared by condensation of the corresponding amides with various aldehydes and p-toluenesulfinic acid, with NaCN has been studied. The outcome of the reaction is strongly d

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 %).

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.

Synthesis and structure-activity relationships of the first ferrocenyl-aryl-hydantoin derivatives of the nonsteroidal antiandrogen nilutamide

We present here the first synthesis of organometallic complexes derived from the nonsteroidal antiandrogen nilutamide, bearing a ferrocenyl substituent at position N(1) or at C(5) of the hydantoin ring; for comparison, we also describe the C(5) p-anisyl organic analogue. All of these complexes retain a modest affinity for the androgen receptor. The N-substituted complexes show a weak or moderate antiproliferative effect (IC50 around 68 μM) on hormone-dependent and -independent prostate cancer cells, while the C(5)-substituted compounds exhibit toxicity levels 10 times higher (IC 50 around 5.4 μM). This strong antiproliferative effect is probably due to a structural effect linked to the aromatic character of the ferrocene rather than to its organometallic feature. In addition, it seems connected to a cytotoxic effect rather than an antihormonal one. These results open the way toward a new family of molecules that are active against both hormone-dependent and hormone-independent prostate cancer cells.

The use of Lewis acids in the synthesis of 5-arylhydantoins

Different Lewis acids are able to promote the Friedel-Crafts reaction between 5-bromohydantoin and aromatic compounds. In the case of phenol, mixtures of ortho and para isomers are always obtained, with Mg(ClO4) 2 leading to the best selectivity. However, the best overall yield of 5-(hydroxyphenyl)hydantoin is obtained with YbCl3. This method can be extended to other aromatic systems such as anisole and thiophene. These reactions give similar yields but proceed with total selectivity to 5-(4-methoxyphenyl)hydantoin and 5-(2-thiophenyl)hydantoin, respectively. The cationic exchange of MgII and YbIII on anionic solid supports allows the preparation of very efficient heterogeneous catalysts for this reaction (productivity up to 600 mol of hydantoin per mole of Mg). These catalysts have practical advantages in that they can be recycled and reused.

Ultrasound-promoted synthesis of 5-substituted and 5,5-disubsntuted hydantoins

Sonication of a mixture of industrial grade sodium cyanide (aqueous solution) and ammonium carbonate in aqueous alcohol with aldehydes or ketones affords the 5-substituted or 5,5-disubstituted hydantoins in 30-92percent yield.

Production of ring-substituted D-phenylglycines by microbial or enzymatic hydrolysis/deracemisation of the corresponding DL-hydantoins

A series of 17 ring-mono and -disubstituted D-phenylglycine derivatives was prepared in high enantiomeric purity by enzymatic hydrolysis and deracemisation of the corresponding DL-hydantoins, using D-hydantoinase activities of microorganisms or purified enzymes, followed by diazotation of the resulting N-carbamyl-D-amino acids. No significant L-hydantoinase activity was found to produce the corresponding L-enantiomers.

Process for preparing 5-arylhydantoins using 5-hydantoin, a halogenating agent and p-phenol

The present invention provides a novel process for the preparation of 5-arylhydantoins as an important intermediate of (D)-arylglycines (e.g., (D)-p-hydroxyphenyl-glycine) useful for the synthesis of semisynthetic penicillines and cephalosporins, the process comprising (i) reacting a 5-unsubstituted hydantoin compound with a halogenating agent and (ii) reacting the resulting product with a p-unsubstituted phenol compound, the hydroxy group of which may be protected, to substitute the 5-position of the hydantoin compound with the phenol compound at the para position.