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dc.creatorTrišović, Nemanja
dc.creatorRadovanović, Lidija
dc.creatorJanjić, Goran
dc.creatorJelić, Stefan
dc.creatorRogan, Jelena
dc.date.accessioned2019-12-19T14:04:48Z
dc.date.available2019-12-19T14:04:48Z
dc.date.issued2019
dc.identifier.issn1528-7483
dc.identifier.issn1528-7505
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/3277
dc.description.abstractA series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N–H···O hydrogen bonds, which further self-organize through pairs of C–H···O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N–H···O hydrogen bonds and C–H···O and C–H···π interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
dc.publisherAmerican Chemical Society (ACS)en
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172023/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/45007/RS//
dc.rightsrestrictedAccess
dc.sourceCrystal Growth & Designen
dc.subjectCrystals
dc.subjectReaction products
dc.subjectCrystal structure
dc.subjectPhenyls
dc.subjectMolecular interactions
dc.titleSubstituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Studyen
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractТришовић, Немања; Јелић, Стефан; Роган, Јелена; Радовановић, Лидија; Јањић, Горан;
dc.rights.holderAmerican Chemical Society
dc.citation.volume19
dc.citation.issue4
dc.citation.spage2163
dc.citation.epage2174
dc.citation.rankM21~
dc.description.otherThe peer-reviewed version: [http://cer.ihtm.bg.ac.rs/handle/123456789/3278]
dc.identifier.doi10.1021/acs.cgd.8b01776
dc.identifier.scopus2-s2.0-85063380000
dc.identifier.wos000463843600019
dc.type.versionpublishedVersion


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