33599-32-5

Usage

Uses

Used in Pharmaceutical Industry:
1-N-BUTYLHYDANTOIN is used as an anticonvulsant drug for its ability to prevent seizures by inhibiting excessive electrical activity in the brain.
Used in Metalworking Industry:
1-N-BUTYLHYDANTOIN is used as a corrosion inhibitor in metalworking fluids to protect metal surfaces from corrosion and extend the life of the equipment.
Used as a Chemical Intermediate:
1-N-BUTYLHYDANTOIN is used as an intermediate in the synthesis of other chemicals, contributing to the production of various compounds for different applications.

InChI:InChI=1/C7H12N2O2/c1-2-3-4-9-5-6(10)8-7(9)11/h2-5H2,1H3,(H,8,10,11)

Upstream product

• 104892-32-2 1-carbethoxymethyl-1-(n-butyl)urea 
• 461-72-3 2,4-imidazolidinedione 
• 542-69-8 1-iodo-butane 
• 3182-83-0 ethyl 2-(n-butyl)aminoacetate 
• 131543-46-9 Glyoxal 
• 592-31-4 1-butyl-urea 
• 590-28-3 potassium cyanate 

Downstream Products

• 171515-72-3 1-Butyl-5-[1-{2-butyl-3-[4-(2-trityl-2H-tetrazol-5-yl)-benzyl]-3H-imidazol-4-yl}-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 171515-73-4 1-Butyl-5-[1-{2-butyl-3-[4-(2-trityl-2H-tetrazol-5-yl)-benzyl]-3H-imidazol-4-yl}-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 160998-29-8 methyl (E)-4-<<2-butyl-5-<(3-butyl-2,5-dioxo-4-imidazolidinylidene)methyl>-1H-imidazol-1-yl>methyl>benzoate 
• 152147-95-0 methyl Z-4'-[[2-butyl-5-[(3-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl][1,1'-biphenyl]-2-carboxylate 
• 1187307-84-1 (Z)-5-(4-chlorobenzylidene)-1-n-butylhydantoin 
• 1187307-83-0 (E)-5-(4-chlorobenzylidene)-1-n-butylhydantoin 
• 1187307-82-9 (Z)-5-benzylidene-1-n-butylhydantoin 
• 1187307-81-8 (E)-5-benzylidene-1-n-butylhydantoin 
• 1344708-84-4 3-benzyl-1-butylimidazolidine-2,4-dione 

Relevant academic research and scientific papers

5-Benzylidene-hydantoins: Synthesis and antiproliferative activity on A549 lung cancer cell line

Benzylidene hydantoins have been recently reported as a new class of EGFR inhibitors. We describe here a simple and efficient methodology for the parallel solution-phase synthesis of a library of 5-benzylidene hydantoins, which were evaluated for antiproliferative activity on the human lung adenocarcinoma A549 cell line. Various substituents at positions 1, 3 and 5 on the hydantoin nucleus were examined. In the presence of a 5-benzylidene group and of a lipophilic substituent at position 1, most of the tested compounds inhibited cell proliferation at a concentration of 20 μM. Compound 7 (UPR1024), bearing 1-phenethyl and (E)-5-p-OH-benzylidene substituents, was found to be the most active derivative of the series. It inhibited EGFR autophosphorylation and induced DNA damage in A549 cells. Compound 7 and other synthesized 5-benzylidene hydantoin derivatives increased p53 levels, suggesting that the dual mechanism of action was a common feature shared by compound 7 and other member of the series.

Inhibitors of cellular necrosis

The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

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.

Process for producing 1-substituted-hydantoins

The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: STR1 wherein R1 represents d hydrocarbon group which may be substituted and others, cheracterized by reacting N-sustituted-N-alkcycarbonylamnilo-acetonitrile of Formula II: STR2 wherein R2 represents an alkyl group and others, with an alkali metal hydroxides or the like and then treating with an acid.

Process for producing 1-substituted-hydantoins

The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: wherein R1represents a hydrocarbon group which may be substituted and others,characterized by reacting N-substituted-N-alkoxycarbonylamino-acetonitrile of Formula II: wherein R2represents an alkyl group and others,with an alkali metal hydroxides or the like and then treating with an acid.

Derivatives of 5-[[1-(4'-carboxybenzyl)imidazolyl]methylidene]hydantoins as orally active angiotensin II receptor antagonists

A series of 5-[[1-(4'-carboxybenzyl)imidazolyl]methylidene]hydantoins have been prepared and evaluated as in vitro and in vivo angiotensin II (Aug II) antagonists. Variation of substituents on the hydantoin ring leads to potent and selective Aug II antagonists with nanomolar IC50 values at the AT1 receptor and negligible affinity for the AT2 receptor. Preferred substituents include an n-butyl at R1 and an alkyl or heteroarylmethyl substituent at R2. The selection of the R2 substituent was guided in part by the calculation of its log P since a significant correlation was observed between CLOGP and AT2 binding affinity. The biphenyl tetrazole pharmacophore, common to a number of AT1 antagonists, could be replaced by, for example, a 4-carbomethoxyphenyl substituent resulting in potent Aug II antagonists both in vitro and in vivo. A representative compound of this series is 57, which reduced the mean arterial blood pressure of renal hypertensive rats by 40% at 30 mg/kg po and by 25% at 10 mg/kg po. In addition this compound was efficacious in the salt-deplete normotensive monkey model maximally decreasing blood pressure 27% at 10 mg/kg po. In summary, these compounds belong to a novel class of Aug II antagonists that lack the biphenyl tetrazole moiety yet display appreciable and long lasting oral activity.

SUBSTITUTED-5-METHYLIDENE HYDANTOINS WITH AT1 RECEPTOR ANTAGONIST PROPERTIES

Substituted 1-benzylimidazole-5-methylidene hydantoins are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and method of using them. Intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, surgically induced vascular smooth muscle proliferation, and glaucoma.

BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID

Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.