Exploring the supramolecular profile of 5-phenylhydantoins

The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N-H O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin ( 1 ) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins ( 2-4 ), were synt...

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Bibliographic Details
Published in:CrystEngComm 2023-06, Vol.25 (25), p.3637-3654
Main Authors: Lazi, Anita, Radovanovi, Lidija, Rogan, Jelena, Valenti, Nataša, Janji, Goran, or evi, Ivana, Trišovi, Nemanja
Format: Article
Language:English
Subjects:
Biological activity
Crystal structure
Crystallization
Hydantoin
Hydrogen bonding
Mathematical analysis
Matrix metalloproteinases
Qualitative analysis
Reductases
Single crystals
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Summary:The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N-H O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin ( 1 ) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins ( 2-4 ), were synthesized by the Bucherer-Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities. Investigation of self-assembly pathways of 5-phenylhydantoins which results either in racemates, racemic hydrate or conglomerates, as well as a docking study on three different targets, is presented.
ISSN:1466-8033
1466-8033
DOI:10.1039/d3ce00213f