Hydantoins: Synthesis, properties and anticonvulsant activity

Trišović, Nemanja; Ušćumlić, Gordana S.; Petrović, Slobodan

doi:10.2298/hemind0901017t

Cited by 5 publications

(3 citation statements)

References 62 publications

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“…Spirohidantoini su bele kristalne supstance, različitih temperatura topljenja. Spirohidantoini sa supstituentima na atomima azota se tope na nižim temperaturama od nesupstituisanih analoga što je posledica manje polarnosti molekula i smanjene mogućnosti građenja intermolekulskih vodoničnih veza [12,13]. Usled velike koncentracije heteroatoma i karbonilnih grupa u prstenu, spirohidantoini su hidrofilni molekuli; dobro se rastvaraju u vodi, etanolu i etil-acetatu [13].…”

Section: Fizička Svojstva Spirohidantoinaunclassified

“…Uspostavljanje vodoničnih veza sa ciljnim mestima nalazi se u osnovi mehanizma njihovog antikonvulzivnog delovanja. Kristalografska analiza antikonvulziva je pokazala da međusobna orijentacija aromatične grupe i dela molekula koji gradi vodonične veze značajno utiče na efikasnost njihovog delovanja [13,[24][25][26].…”

Section: Derivati Spirohidantoina Sa Antikonvulzivnim Svojstvimaunclassified

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Synthesis, structure and biological properties of active spirohydantoin derivatives

Lazić¹,

Valentić²,

Trišović³

et al. 2016

Hem Ind

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Spirohidantoins represent an pharmacologically important class of heterocycles since many derivatives have been recognized that display interesting activities against a wide range of biological targets. First synthesis of cycloalkanespiro-5-hydantoins was performed by Bucherer and Lieb 1934 by the reaction of cycloalkanone, potassium cyanide and ammonium-carbonate at reflux in a mixture of ethanol and water. QSAR (Quantitative Structure-Activity Relationship) studies showed that a wide range of biological activities of spirohydantoin derivatives strongly depend upon their structure. This paper describes different methods of synthesis of spirohydantoin derivatives, their physico-chemical properties and biological activity. It emphasizes the importance of cycloalkanespiro-5-hydantoins with anticonvulsant, antiproliferative, antipsychotic, antimicrobial and antiinflammatory properties as well as their importance in the treatment of diabetes. Numerous spirohydantoin compounds exhibit physiological activity such as serotonin and fibrinogen antagonist, inhibitors of the glycine binding site of the NMDA receptor also, antagonist of leukocyte cell adhesion, acting as allosteric inhibitors of the protein-protein interactions. Some spirohydantoin derivatives have been identified as antitumor agents. Their activity depends on the substituent presented at position N-3 of the hydantoin ring and increases in order alkene > ester > ether. Besides that, compounds that contain two electron withdrawing groups (e.g. fluorine or chlorine) on the third and fourth position of the phenyl ring are better antitumor agents than compounds with a single electron withdrawing group. [Projekat Ministarstva nauke Republike Srbije, br. 172013]

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Section: Fizička Svojstva Spirohidantoinaunclassified

Section: Derivati Spirohidantoina Sa Antikonvulzivnim Svojstvimaunclassified

Synthesis, structure and biological properties of active spirohydantoin derivatives

Lazić¹,

Valentić²,

Trišović³

et al. 2016

Hem Ind

Self Cite

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“…Aside from them being synthetically attractive, hydantoins exhibit a wide range of biological activity [6][7][8][9]. Some of the attributed biological properties include antimicrobial, antitumor, antiandrogen, antiteratogenic, hypnotic, antiepileptic and anticonvulsant activity, wound healing, muscle relaxant, treatment of cachexia, psoriasis, chorea, anoxia, tuberculosis and some infectious diseases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Various Amino Acid Derived Thiohydantoins

Stanić

Živković

Šmit

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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Hydantoins and their sulfur containing analogues, thiohydantoins, are cyclic ureides that have attracted huge attention ever since their discovery. Most of them are biologically active compounds and several points of structural diversity have made them very synthetically attractive. Although substituents can be introduced to the hydantoin nucleus, most substituted hydantoins are synthesized from substrates already containing these groups, while forming the hydantoin nucleus. This is a common route to the synthesis of hydantoins and one of them is employed in this study. A series of 3-allyl-2-thiohydantoins is synthesized from various α-amino acids in a reaction with allyl isothiocyanate. The substitution of the acquired thiohydantoin depends on the structure of the starting α-amino acid. The residual group of the α-amino acid becomes the substituent at the C5-position, while N-monosubstituted amino acids give rise to a substituent in the N1-position. The reaction is carried out in a two-step process and the reaction conditions generally depend on the nature of the amino acid itself. All thiohydantoins are obtained in a good yield and fully characterized by NMR and IR spectroscopy, as well as X-ray crystallography.

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Thermolysis reactions of N-alkyl-N′-CBZ amino acid amides. A route to substituted imidazolidine-2,4-diones

Casale

Hunt

2018

Tetrahedron Letters

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Hydantoins: Synthesis, properties and anticonvulsant activity

Cited by 5 publications

References 62 publications

Synthesis, structure and biological properties of active spirohydantoin derivatives

Synthesis, structure and biological properties of active spirohydantoin derivatives

Synthesis and Characterization of Various Amino Acid Derived Thiohydantoins

Thermolysis reactions of N-alkyl-N′-CBZ amino acid amides. A route to substituted imidazolidine-2,4-diones

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