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Usage

Uses

Used in Pharmaceutical Industry:
1-METHYLHYDANTOIN is used as a reactant for organocatalytic tandem three-component reactions involving aldehyde, alkyl vinyl ketone, and amide. This reaction is crucial for the synthesis of complex molecules with potential pharmaceutical applications.
1-METHYLHYDANTOIN is used as a reactant for the synthesis of selective angiotensin II AT2 receptor agonists. These agonists have reduced CYP 450 inhibition, making them more effective and safer for the treatment of various cardiovascular conditions.
1-METHYLHYDANTOIN is used as a reactant for the synthesis of allosteric glucokinase activators. These activators play a significant role in the regulation of glucose metabolism and have potential applications in the treatment of diabetes.
1-METHYLHYDANTOIN is used as a reactant for the synthesis of hydantoin derivatives with antiproliferative activity. These derivatives have potential applications in cancer therapy, as they can inhibit the growth and proliferation of cancer cells.
1-METHYLHYDANTOIN is used as a reactant for the synthesis of thiohydantoins. Thiohydantoins are a class of compounds with diverse biological activities, including antimicrobial, antiviral, and anticancer properties.
1-METHYLHYDANTOIN is used as a reactant for the synthesis of P2X7 receptor antagonists. These antagonists have potential applications in the treatment of inflammatory and neurodegenerative diseases, as they can modulate the activity of the P2X7 receptor, which is involved in various physiological and pathological processes.

Metabolic pathway

The metabolic pathway of 1-methylhydantoin via 5-hydroxy-1-methylhydantoin, methylparabanic acid, and 5-N-methyloxaluric acid proves to be a major and general metabolic pathway in rabbits.

InChI:InChI=1/C4H6N2O2/c1-6-3(7)2-5-4(6)8/h2H2,1H3,(H,5,8)

Upstream product

• 60-27-5 creatinine 
• 590-28-3 potassium cyanate 
• 107-97-1 sarcosine 
• 67792-96-5 N-carbamoyl-alanine ethyl ester 
• 77340-50-2 N-carbamoyl-DL-alanine 
• 111184-59-9 3-methylhydantoic acid nitrile 
• 30565-25-4 N-carbamoylsarcosine 
• 57-13-6 urea 
• 506-77-4 cyanogen chloride 
• 111184-53-3 N-Methyl-2-(1-methyl-ureido)-acetamide 
• 104892-31-1 (1-Methyl-ureido)-acetic acid ethyl ester 
• 111184-52-2 3-methylhydantoinamide 
• 84210-26-4 1-methyl-5-hydroxy-imidazoline-2,4-dione 
• 60-27-5 Creatinine 

Downstream Products

• 55441-71-9 9-methyluric acid 
• 31113-70-9 5-(benzylidene)-1-methylhydantoin 
• 109133-77-9 1-Methyl-5-[1-(5-methyl-2-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 122060-59-7 (Z)-1-methyl-5-(4-nitrophenyl)methylenehydantoin 
• 116672-34-5 (E)-1-methyl-5-(4-nitrophenyl)methylenehydantoin 
• 3985-40-8 1-methyl-5-(2-nitro-benzylidene)-imidazolidine-2,4-dione 
• 204072-94-6 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-(3N-methylhydanto-1N-yl)pyrrolidine 
• 204072-99-1 (2R,4S)-1-[4-(2-Methoxy-ethoxy)-benzenesulfonyl]-4-(3-methyl-2,5-dioxo-imidazolidin-1-yl)-pyrrolidine-2-carboxylic acid methyl ester 
• 204073-00-7 (2R,4S)-4-(3-Methyl-2,5-dioxo-imidazolidin-1-yl)-1-(4-phenoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 204072-95-7 (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(3-methyl-2,5-dioxo-imidazolidin-1-yl)-pyrrolidine-2-carboxylic acid methyl ester 
• 1028091-05-5 1-methyl-5-[1-(2-pyrrolidin-1-yl-phenyl)-methyl(Z)-ylidene]-imidazolidine-2,4-dione 
• 1028091-07-7 1-methyl-5-[1-(2-pyrrolidin-1-yl-phenyl)-methy-(E)-ylidene]-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”

Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

Discovery of a bacterial 5-methylcytosine deaminase

5-Methylcytosine is found in all domains of life, but the bacterial cytosine deaminase from Escherichia coli (CodA) will not accept 5-methylcytosine as a substrate. Since significant amounts of 5-methylcytosine are produced in both prokaryotes and eukaryotes, this compound must eventually be catabolized and the fragments recycled by enzymes that have yet to be identified. We therefore initiated a comprehensive phylogenetic screen for enzymes that may be capable of deaminating 5-methylcytosine to thymine. From a systematic analysis of sequence homologues of CodA from thousands of bacterial species, we identified putative cytosine deaminases where a "discriminating" residue in the active site, corresponding to Asp-314 in CodA from E. coli, was no longer conserved. Representative examples from Klebsiella pneumoniae (locus tag: Kpn00632), Rhodobacter sphaeroides (locus tag: Rsp0341), and Corynebacterium glutamicum (locus tag: NCgl0075) were demonstrated to efficiently deaminate 5-methylcytosine to thymine with values of kcat/Km of 1.4 × 105, 2.9 × 104, and 1.1 × 103 M-1 s-1, respectively. These three enzymes also catalyze the deamination of 5-fluorocytosine to 5-fluorouracil with values of kcat/Km of 1.2 × 105, 6.8 × 104, and 2.0 × 102 M-1 s-1, respectively. The three-dimensional structure of Kpn00632 was determined by X-ray diffraction methods with 5-methylcytosine (PDB id: 4R85), 5-fluorocytosine (PDB id: 4R88), and phosphonocytosine (PDB id: 4R7W) bound in the active site. When thymine auxotrophs of E. coli express these enzymes, they are capable of growth in media lacking thymine when supplemented with 5-methylcytosine. Expression of these enzymes in E. coli is toxic in the presence of 5-fluorocytosine, due to the efficient transformation to 5-fluorouracil.

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

Synthesis and evaluation of anti-inflammatory and antitussive activity of hydantion derivatives

1-Methylhydantion is a compound, which was isolated from Oviductus Ranae for the first time. In our study, we found that it showed good antitussive and anti-inflammatory activity. It is also the first report which illustrates the antitussive activity of hydantion derivative. A series of hydantion derivatives were synthesized and evaluated for their anti-inflammatory and antitussive activity in vivo. The pharmacological tests showed that compounds 7a, 7c and 7d have good anti-inflammatory and antitussive activity compared to Ibuprofen and codeine. Compound 7a in particular showed two-fold stronger anti-inflammatory activity than Ibuprofen.

Facile synthesis of hydantoins and thiohydantoins in aqueous solution

A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Synthesis of a new isomer of creatinine and its use in the preparation of the food mutagen 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PHIP)

Base-induced cyclization of N′-cyanomethyl-N′-methylurea gives 1-methyl-4-amino-imidazol-2-one, this in turn is condensed with 3-hydroxy-2-phenylacrolein to yield an imidazo[4,5-b]pyridine which is converted into 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PHIP).

A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.

α-Ureidoalkylation of thiosemicarbazide and aminoguanidine

Optimum conditions for the targeted synthesis of 5,7-dialkyl-3- thioxoperhydroimid-azo[4,5-e][1,2,4]triazin-6-ones, 4,5-bis(3- thiosemicarbazido(guanidinoamino))imidazolidin-2-ones, and 1,3-dialkyl-4- (guanidinoimino)imidazolidin-2-ones by α-ureidoalkylation of thiosemicarbazide or aminoguanidine were found. A novel conglomerate in the series of imidazolidin-2-one derivatives was detected: 4,5-bis(guanidinoamino)- 1,3-dimethylimid-azolidin-2-one dihydrochloride dihydrate. Springer Science+Business Media, Inc. 2006.

Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils

Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.