Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone

Abstract

The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7- benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo and heterochiral dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a bigger number of the contacts in the environment of the tetralin unit results from its larger contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall stabilization. In addition, the investigated compound is identified as a potential inhibitor of kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy benzyl units revealed that interactions with nonpolar groups are the most prevalent and even more numerous than interactions with other amino acid residues (polar, positive and negative).