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

ChemPlusChem
Anita M LazićNemanja P Trišović

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...Continue Reading

References

Dec 11, 1999·Nucleic Acids Research·H M BermanP E Bourne
May 7, 2002·Il Farmaco·Emilia NaydenovaBoris Aleksiev
May 31, 2002·Acta Crystallographica. Section B, Structural Science·Ian J BrunoRobin Taylor
Aug 4, 2004·Archives of Biochemistry and Biophysics·Hisashi SuzukiAllan E Rettie
Feb 23, 2010·Bioorganic & Medicinal Chemistry Letters·Wensheng YuGuowei Zhou
Jul 21, 2010·Molecular Pharmacology·Gregory M Lipkind, Harry A Fozzard
Nov 23, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Dragan B NinkovićSnežana D Zarić
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jan 23, 2016·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Lionel SacconnayAlessandra Nurisso
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Oct 21, 2016·Frontiers in Neuroscience·Samuele MaramaiMargherita Brindisi
Jan 10, 2019·European Journal of Medicinal Chemistry·SeoHyun ChoDongyun Shin
Jul 18, 2019·ACS Medicinal Chemistry Letters·Joao NunesNiall A Anderson

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