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dc.contributor.authorAntoniadis, C. D.en
dc.contributor.authorHadjikakou, S. K.en
dc.contributor.authorHadjiliadis, N.en
dc.contributor.authorPapakyriakou, A.en
dc.contributor.authorBaril, M.en
dc.contributor.authorButler, I. S.en
dc.rightsDefault Licence-
dc.subjectbioinorganic chemistryen
dc.subjectcharge-transfer complexesen
dc.subjectheterocyclic selenoamidesen
dc.subjectiodine adductsen
dc.subjecti iodothyronine deiodinaseen
dc.subjectthyroid-hormone synthesisen
dc.subjectray crystal-structuresen
dc.subjecttransfer complexesen
dc.subjectspectroscopic characterizationen
dc.subjectmolecular adductsen
dc.subjectselenium analogen
dc.titleSynthesis and structures of Se analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives: Formation of dimeric Se-Se compounds and deselenation reactions of charge-transfer adducts of diiodineen
heal.type.enJournal articleen
heal.type.elΆρθρο Περιοδικούel
heal.identifier.primaryDOI 10.1002/chem.200501455-
heal.identifier.secondary<Go to ISI>://000240387000016-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.abstractFour selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil (PTU), of formulae RSeU, (R = methyl (Me) (1), ethyl (Et) (2), n-propyl (nPr) (3), and isopropyl (iPr) 4), have been synthesized. Reaction of 1-4 with diiodine in a 1:1 molar ratio in dichloromethane results in the formation of [(RSeU)I(2)] (R = methyl (5), ethyl (6), n-propyl (7) and isopropyl (8)). All compounds have been characterized by elemental analysis, FT-Raman, FT-IR, UV/Vis, (1)H-, (13)C-, (77)Se-1D and -2D NMR spectroscopy, and ESI-MS spectrometric techniques. Recrystallization of 4 from dichloromethane afforded (4 center dot CH(2)Cl(2))- Crystals of [(nPrSeU)I(2)] (7), a charge-transfer complex, were obtained from chloroform solutions, while crystallization of 6 and 7 from acetone afforded the diselenides [N-(6-Et-4-pyrimidone)(6-EtSeU)(2)] (9 center dot 2H(2)O) and [N-(6-nPr-4-pyrimidone)(6-nPrSeU)(2)] (10) as oxidation products. Recrystallization of 7 from methanol/acetonitrile solutions led to deselenation with the formation of 6-n-propyl-2-uracil (nPrU) (11). [(nPrSeU)I(2)] (7) was found to be a charge-transfer complex with a Se-I bond. These results are discussed in relation to the mechanism of action of antithyroid drugs.en
heal.publisherWiley-VCH Verlagen
heal.journalNameChemistry-a European Journalen
heal.journalTypepeer reviewed-
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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