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dc.creatorLazić, Anita
dc.creatorĐorđević, Ivana
dc.creatorRadovanović, Lidija
dc.creatorPopović, Dragan
dc.creatorRogan, Jelena
dc.creatorJanjić, Goran
dc.creatorTrišović, Nemanja
dc.date.accessioned2021-03-10T14:23:09Z
dc.date.available2021-03-10T14:23:09Z
dc.date.issued2020
dc.identifier.issn2192-6506
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/4504
dc.description.abstractA 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...pi 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...pi, 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.en
dc.publisherWiley-VCH Verlag Gmbh, Weinheim
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200135/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200287/RS//
dc.rightsrestrictedAccess
dc.sourceChempluschem
dc.subjectchiral recognitionen
dc.subjectdrugsen
dc.subjectfragment-based analysisen
dc.subjectmolecular dockingen
dc.subjectnoncovalent interactionsen
dc.titleSelf-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactionsen
dc.typearticle
dc.rights.licenseARR
dc.citation.epage1232
dc.citation.issue6
dc.citation.other85(6): 1220-1232
dc.citation.rankM22~
dc.citation.spage1220
dc.citation.volume85
dc.identifier.doi10.1002/cplu.202000273
dc.identifier.pmid32515167
dc.identifier.rcubconv_6150
dc.identifier.scopus2-s2.0-85086356663
dc.identifier.wos000544057700017
dc.type.versionpublishedVersion


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