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dc.creatorLazić, Anita M.
dc.creatorRadovanović, Lidija D.
dc.creatorBožić, Bojan
dc.creatorBožić, Nedeljković B.
dc.creatorVitnik, Vesna
dc.creatorVitnik, Željko
dc.creatorRogan, Jelena R.
dc.creatorValentić, Nataša V.
dc.creatorUšćumlić, Gordana
dc.creatorTrišović, Nemanja
dc.date.accessioned2019-01-30T18:01:37Z
dc.date.available2019-01-30T18:01:37Z
dc.date.issued2019
dc.identifier.issn0022-2860
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2489
dc.description.abstractTwo series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.en
dc.publisherElsevier B.V.
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173052/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/45007/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Molecular Structure
dc.subjectAntiproliferative activityen
dc.subjectDFT calculationen
dc.subjectSpirohydantoinen
dc.subjectX-ray structure determinationen
dc.titleSynthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moietyen
dc.typearticle
dc.rights.licenseARR
dc.citation.volume1180
dc.citation.spage48
dc.citation.epage62
dc.citation.other1180: 48-62
dc.citation.rankM22~
dc.identifier.doi10.1016/j.molstruc.2018.11.071
dc.identifier.rcubConv_4494
dc.identifier.scopus2-s2.0-85059311562
dc.identifier.wos000457660300007
dc.type.versionpublishedVersion


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