Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions
Autor: | Anita Lazić, Nemanja Trišović, Jelena Rogan, Lidija Radovanović, Ivana S. Đorđević, Dragan Popovic, Goran V. Janjić |
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Jazyk: | angličtina |
Rok vydání: | 2020 |
Předmět: |
Chiral recognition
Tetrahydronaphthalenes Noncovalent interactions Stereochemistry Cooperativity Crystal structure 010402 general chemistry Crystallography X-Ray 01 natural sciences chemistry.chemical_compound Tetralone Non-covalent interactions Humans Spiro Compounds Tetralin chemistry.chemical_classification 010405 organic chemistry Hydantoins Fragment-based analysis Intermolecular force Receptors Dopamine D3 Drugs Stereoisomerism General Chemistry Interaction energy 0104 chemical sciences Molecular Docking Simulation Interleukin-1 Receptor-Associated Kinases chemistry Molecular docking Enantiomer |
Zdroj: | ChemPlusChem Chempluschem |
Popis: | 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. 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] |
Databáze: | OpenAIRE |
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