Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative

Abstract

A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the presence of different intermolecular interactions. A hallmark structural feature of the investigated compound was alternation of double layers. A larger number of the contact fragments in the environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl unit provides a slightly greater contribution to the overall stabilization. Regarding the pharmacological potential of the investigated compound, we performed a docking study on the dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.