Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions
Samo za registrovane korisnike
2020
Autori
Lazić, Anita
Đorđević, Ivana

Radovanović, Lidija

Popović, Dragan

Rogan, Jelena

Janjić, Goran

Trišović, Nemanja

Članak u časopisu (Objavljena verzija)

Metapodaci
Prikaz svih podataka o dokumentuApstrakt
A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater cont...ribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.
Ključne reči:
chiral recognition / drugs / fragment-based analysis / molecular docking / noncovalent interactionsIzvor:
Chempluschem, 2020, 85, 6, 1220-1232Izdavač:
- Wiley-VCH Verlag Gmbh, Weinheim
Finansiranje / projekti:
- Ministarstvo prosvete, nauke i tehnološkog razvoja Republike Srbije, Ugovor br. 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-200026)
- Ministarstvo prosvete, nauke i tehnološkog razvoja Republike Srbije, Ugovor br. 200135 (Univerzitet u Beogradu, Tehnološko-metalurški fakultet) (RS-200135)
- Ministarstvo prosvete, nauke i tehnološkog razvoja Republike Srbije, Ugovor br. 200287 (Inovacioni centar Tehnološko-metalurškog fakulteta u Beogradu doo) (RS-200287)
DOI: 10.1002/cplu.202000273
ISSN: 2192-6506
PubMed: 32515167
WoS: 000544057700017
Scopus: 2-s2.0-85086356663
Kolekcije
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Lazić, Anita AU - Đorđević, Ivana AU - Radovanović, Lidija AU - Popović, Dragan AU - Rogan, Jelena AU - Janjić, Goran AU - Trišović, Nemanja PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4504 AB - A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit. PB - Wiley-VCH Verlag Gmbh, Weinheim T2 - Chempluschem T1 - Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions EP - 1232 IS - 6 SP - 1220 VL - 85 DO - 10.1002/cplu.202000273 ER -
@article{ author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja", year = "2020", abstract = "A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.", publisher = "Wiley-VCH Verlag Gmbh, Weinheim", journal = "Chempluschem", title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions", pages = "1232-1220", number = "6", volume = "85", doi = "10.1002/cplu.202000273" }
Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Janjić, G.,& Trišović, N.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem Wiley-VCH Verlag Gmbh, Weinheim., 85(6), 1220-1232. https://doi.org/10.1002/cplu.202000273
Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Janjić G, Trišović N. Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem. 2020;85(6):1220-1232. doi:10.1002/cplu.202000273 .
Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions" in Chempluschem, 85, no. 6 (2020):1220-1232, https://doi.org/10.1002/cplu.202000273 . .