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dc.contributor.authorStucchi, M.en_US
dc.contributor.authorCairati, S.en_US
dc.contributor.authorCetin-Atalay, R.en_US
dc.contributor.authorChristodoulou, M.S.en_US
dc.contributor.authorGrazioso G.en_US
dc.contributor.authorPescitelli G.en_US
dc.contributor.authorSilvani, A.en_US
dc.contributor.authorYildirim, D.C.en_US
dc.contributor.authorLesma G.en_US
dc.date.accessioned2016-02-08T09:53:44Z
dc.date.available2016-02-08T09:53:44Z
dc.date.issued2015en_US
dc.identifier.issn14770520
dc.identifier.urihttp://hdl.handle.net/11693/21970
dc.description.abstractThe concurrent employment of α-amino acid-derived chiral components such as aldehydes and α-isocyanoacetates, in a sequential Ugi reaction/cyclization two-step strategy, opens the door to the synthesis of three structurally distinct piperazine-based scaffolds, characterized by the presence of l-Ala and/or l-Phe-derived side chains and bearing appropriate functionalities to be easily applied in peptide chemistry. By means of computational studies, these scaffolds have been demonstrated to act as minimalist peptidomimetics, able to mimic a well defined range of peptide secondary structures and therefore potentially useful for the synthesis of small-molecule PPI modulators. Preliminary biological evaluation of two different resistant hepatocellular carcinoma cellular lines, for which differentiation versus resistance ability seem to be strongly correlated with well defined types of PPIs, has revealed a promising antiproliferative activity for selected compounds. © The Royal Society of Chemistry 2015.en_US
dc.language.isoEnglishen_US
dc.source.titleOrganic and Biomolecular Chemistryen_US
dc.relation.isversionofhttp://dx.doi.org/10.1039/c5ob00218den_US
dc.subjectAmino acidsen_US
dc.subjectChemical reactionsen_US
dc.subjectMobile securityen_US
dc.subjectPeptidesen_US
dc.subjectStereochemistryen_US
dc.subjectAlpha-amino acidsen_US
dc.subjectAnti-proliferative activitiesen_US
dc.subjectBiological evaluationen_US
dc.subjectComputational studiesen_US
dc.subjectHepatocellular carcinomaen_US
dc.subjectPeptide chemistriesen_US
dc.subjectPeptide secondary structuresen_US
dc.subjectSmall moleculesen_US
dc.subjectSynthesis (chemical)en_US
dc.subjectalanineen_US
dc.subjectpeptidomimetic agenten_US
dc.subjectphenylalanineen_US
dc.subjectpiperazineen_US
dc.subjectpiperazine derivativeen_US
dc.subjectcell differentiationen_US
dc.subjectcell proliferationen_US
dc.subjectchemistryen_US
dc.subjectconformationen_US
dc.subjectcyclizationen_US
dc.subjectdose responseen_US
dc.subjectdrug effectsen_US
dc.subjecthumanen_US
dc.subjectquantum theoryen_US
dc.subjectstructure activity relationen_US
dc.subjectsynthesisen_US
dc.subjecttumor cell lineen_US
dc.subjectAlanineen_US
dc.subjectCell Differentiationen_US
dc.subjectCell Line, Tumoren_US
dc.subjectCell Proliferationen_US
dc.subjectCyclizationen_US
dc.subjectDose-Response Relationship, Drugen_US
dc.subjectHumansen_US
dc.subjectMolecular Conformationen_US
dc.subjectPeptidomimeticsen_US
dc.subjectPhenylalanineen_US
dc.subjectPiperazinesen_US
dc.subjectQuantum Theoryen_US
dc.subjectStructure-Activity Relationshipen_US
dc.titleApplication of the Ugi reaction with multiple amino acid-derived components: Synthesis and conformational evaluation of piperazine-based minimalist peptidomimeticsen_US
dc.typeArticleen_US
dc.departmentDepartment of Molecular Biology and Genetics
dc.citation.spage4993en_US
dc.citation.epage5005en_US
dc.citation.volumeNumber13en_US
dc.citation.issueNumber17en_US
dc.identifier.doi10.1039/c5ob00218den_US
dc.publisherRoyal Society of Chemistryen_US


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