Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins

Hmuda, Sleem F.; Trišović, Nemanja; Valentić, Nataša V.; Ušćumlić, Gordana S.

doi:10.1007/s10953-010-9641-7

Cited by 7 publications

(4 citation statements)

References 24 publications

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“…Specific solute-solvent interactions were subdivided into solvent Lewis-basicity interactions (hydrogen bond donor (HBD) solute/ /(hydrogen bond acceptor (HBA) solvents) and solvent Lewis acidity interactions (hydrogen bond acceptor (HBA) solute/(hydrogen bond donor (HBD) solvents). Thus, the following multiparameter equation was suggested for application in linear solvation energy relationships (LSER): [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] LSER have been used in various fields, such as, ionic liquids, solubility, thermochemistry, NMR chemical shifts, pharmaceuticals, etc. Equation (10) has been used in the correlation analysis by multiple regression of numerous reaction rates and equilibria, spectroscopic data and various other solvent dependent processes.…”

Section: Application Of the Kat Model For The Study Of The Solvent Efmentioning

confidence: 99%

Complexation of molybdenum(VI) with methyliminodiacetic acid in different water + methanol solutions

Zeighaminezhad

Majlesi

2016

JSCS

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The complexation of molybdenum(VI) with methyliminodiacetic acid (MIDA) at pH 6.00, T = 298 K, I = 0.1 mol dm-3 of sodium chloride and different water + methanol solutions (0-45 vol. %) was studied using potentiometric and UV spectrophotometric measurements. The values of the stability constants were calculated and their trends interpreted using the Kamlet-Abboud-Taft (KAT) model in order to investigate the role of different specific and non-specific interactions in aqueous solutions of methanol.

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Section: Application Of the Kat Model For The Study Of The Solvent Efmentioning

confidence: 99%

Complexation of molybdenum(VI) with methyliminodiacetic acid in different water + methanol solutions

Zeighaminezhad

Majlesi

2016

JSCS

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“…Proučavajući antiproliferativnu aktivnost 3-(4-supstituisanih benzil)-5,5-difenilhidantoina i 3-(4-supstituisanih benzil)-5-etil-5-fenilhidantoina, Ušćumlić i saradnici su pokazali značajnu aktivnost ovih molekula prema ćelijskoj liniji humanog karcinoma dojke, MDA--MB-231 i ćelijskoj liniji humanog karcinoma kolona HCT-116. Aktivnost je naročito izražena kada se na fenilnom jezgru kao supstituenti nalaze metil-grupa i halogeni elementi [39][40][41][42].…”

Section: Antiproliferativna Aktivnost Derivata Spirohidantoinaunclassified

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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“…Poupaert et al tested a limited series of compounds structurally related to phenytoin and observed that the anticonvulsant activity decreased with a reduction in their ability to form hydrogen bonds. [12][13][14] Since most drug candidates fail in preclinical and clinical trials because of their unfavourable ADME (absorption, distribution, metabolism and excretion) properties, ADME modelling has attracted significant attention over the last two decades. 10,11 In this context, it was proposed that the structure-activity and structure-property relationships of hydantoin anticonvulsants have molecular size and hydrogen bonding as their primary determinants.…”

Section: Introductionmentioning

confidence: 99%

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

Hmuda¹,

Banjac

Trišović³

et al. 2013

JSCS

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To obtain an 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 nonspecific solvent-solute interactions were correlated with the corresponding 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 solvent-solute interactions and the structure-activity parameters. [Projekat Ministarstva nauke Republike Srbije, br. 172013

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Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins

Cited by 7 publications

References 24 publications

Complexation of molybdenum(VI) with methyliminodiacetic acid in different water + methanol solutions

Complexation of molybdenum(VI) with methyliminodiacetic acid in different water + methanol solutions

Synthesis, structure and biological properties of active spirohydantoin derivatives

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

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