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

Authorized Users Only
2020
Authors
Lazić, Anita M.
Đorđević, Ivana
Radovanović, Lidija
Popović, Dragan
Rogan, Jelena R.
Janjić, Goran
Trišović, Nemanja
Article (Accepted Version)
,
John Wiley and Sons Inc
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⋅⋅⋅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.

Keywords:
Chiral recognition / Drugs / Fragment-based analysis / Molecular docking / Noncovalent interactions
Source:
ChemPlusChem, 2020, 85, 6, 1220-1232
Publisher:
  • John Wiley and Sons Inc.
Projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-200135)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-200287)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-200026)
Note:
  • 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

WoS: 000544057700017

Scopus: 2-s2.0-8508635666
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3716
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