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Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions

Authorized Users Only
2020
Authors
Lazić, Anita
Đorđević, Ivana
Radovanović, Lidija
Popović, Dragan
Rogan, Jelena
Janjić, Goran
Trišović, Nemanja
Article (Published version)
Metadata
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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 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.

Keywords:
chiral recognition / drugs / fragment-based analysis / molecular docking / noncovalent interactions
Source:
Chempluschem, 2020, 85, 6, 1220-1232
Publisher:
  • Wiley-VCH Verlag Gmbh, Weinheim
Funding / projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-200026)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-200135)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-200287)

DOI: 10.1002/cplu.202000273

ISSN: 2192-6506

PubMed: 32515167

WoS: 000544057700017

Scopus: 2-s2.0-85086356663
[ Google Scholar ]
3
1
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4504
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
  • Radovi istraživača (Inovacioni centar) / Researchers’ publications (Innovation Centre)
Institution/Community
Tehnološko-metalurški fakultet
TY  - 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 . .

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