Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions
Autori
Lazić, Anita M.Đorđević, Ivana
Radovanović, Lidija
Popović, Dragan
Rogan, Jelena R.
Janjić, Goran
Trišović, Nemanja
Članak u časopisu (Recenzirana 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⋅⋅⋅π 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⋅⋅⋅π, 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 contri...bution 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:
- John Wiley and Sons Inc.
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200135 (Univerzitet u Beogradu, Tehnološko-metalurški fakultet) (RS-200135)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200287 (Inovacioni centar Tehnološko-metalurškog fakulteta u Beogradu doo) (RS-200287)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-200026)
Napomena:
- This is the peer-reviewed version of the article: Anita M. Lazić, Ivana S. Đorđević, Lidija D. Radovanović, Dragan M. Popović, Jelena R. Rogan, Goran V. Janjić, Nemanja P. Trišović, Self-Assembly and Biorecognition of a Spirohydantoin derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions, ChemPlusChem, 2020, 85, 6, 1220-1232, doi: https://doi.org/10.1002/cplu.202000273
- The published version: https://cer.ihtm.bg.ac.rs/handle/123456789/3638
DOI: 10.1002/cplu.202000273
ISSN: 2192-6506
PubMed: 32515167
WoS: 000544057700017
Scopus: 2-s2.0-85086356663
Institucija/grupa
IHTMTY - JOUR AU - Lazić, Anita M. AU - Đorđević, Ivana AU - Radovanović, Lidija AU - Popović, Dragan AU - Rogan, Jelena R. AU - Janjić, Goran AU - Trišović, Nemanja PY - 2020 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3716 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⋅⋅⋅π 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⋅⋅⋅π, 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 - John Wiley and Sons Inc. T2 - ChemPlusChem T1 - Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions VL - 85 IS - 6 SP - 1220 EP - 1232 DO - 10.1002/cplu.202000273 ER -
@article{ author = "Lazić, Anita M. and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena R. 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⋅⋅⋅π 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⋅⋅⋅π, 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 = "John Wiley and Sons Inc.", journal = "ChemPlusChem", title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions", volume = "85", number = "6", pages = "1220-1232", doi = "10.1002/cplu.202000273" }
Lazić, A. M., Đorđević, I., Radovanović, L., Popović, D., Rogan, J. R., Janjić, G.,& Trišović, N.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem John Wiley and Sons Inc.., 85(6), 1220-1232. https://doi.org/10.1002/cplu.202000273
Lazić AM, Đorđević I, Radovanović L, Popović D, Rogan JR, Janjić G, Trišović N. Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem. 2020;85(6):1220-1232. doi:10.1002/cplu.202000273 .
Lazić, Anita M., Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena R., Janjić, Goran, Trišović, Nemanja, "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions" in ChemPlusChem, 85, no. 6 (2020):1220-1232, https://doi.org/10.1002/cplu.202000273 . .