Exploring the supramolecular profile of 5-phenylhydantoins
Samo za registrovane korisnike
2023
Autori
Lazić, AnitaRadovanović, Lidija
Rogan, Jelena
Valentić, Nataša
Janjić, Goran
Đorđević, Ivana
Trišović, Nemanja
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Izvor:
CrystEngComm, 2023, 25, 25, 3637-3654Izdavač:
- Royal Society of Chemistry
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200135 (Univerzitet u Beogradu, Tehnološko-metalurški fakultet) (RS-MESTD-inst-2020-200135)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200287 (Inovacioni centar Tehnološko-metalurškog fakulteta u Beogradu doo) (RS-MESTD-inst-2020-200287)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-MESTD-inst-2020-200026)
Kolekcije
Institucija/grupa
Inovacioni centarTY - JOUR AU - Lazić, Anita AU - Radovanović, Lidija AU - Rogan, Jelena AU - Valentić, Nataša AU - Janjić, Goran AU - Đorđević, Ivana AU - Trišović, Nemanja PY - 2023 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6504 AB - 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. PB - Royal Society of Chemistry T2 - CrystEngComm T1 - Exploring the supramolecular profile of 5-phenylhydantoins EP - 3654 IS - 25 SP - 3637 VL - 25 DO - 10.1039/d3ce00213f ER -
@article{ author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Valentić, Nataša and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja", year = "2023", abstract = "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.", publisher = "Royal Society of Chemistry", journal = "CrystEngComm", title = "Exploring the supramolecular profile of 5-phenylhydantoins", pages = "3654-3637", number = "25", volume = "25", doi = "10.1039/d3ce00213f" }
Lazić, A., Radovanović, L., Rogan, J., Valentić, N., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm Royal Society of Chemistry., 25(25), 3637-3654. https://doi.org/10.1039/d3ce00213f
Lazić A, Radovanović L, Rogan J, Valentić N, Janjić G, Đorđević I, Trišović N. Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm. 2023;25(25):3637-3654. doi:10.1039/d3ce00213f .
Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Valentić, Nataša, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Exploring the supramolecular profile of 5-phenylhydantoins" in CrystEngComm, 25, no. 25 (2023):3637-3654, https://doi.org/10.1039/d3ce00213f . .