Synthesis and characterization of (PTU)I-2 (PTU=6-n-propyl-2-thiouracil) and (CMBZT)I-2 (CMBZT=5-chloro-2-mercaptobenzothiazole) and possible implications for the mechanism of action of anti-thyroid drugs

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dc.contributor.authorAntoniadis, C. D.en
dc.contributor.authorCorban, G. J.en
dc.contributor.authorHadjikakou, S. K.en
dc.contributor.authorHadjiliadis, N.en
dc.contributor.authorKubicki, M.en
dc.contributor.authorWarner, S.en
dc.contributor.authorButler, I. S.en
dc.date.accessioned2015-11-24T16:48:55Z
dc.date.available2015-11-24T16:48:55Z
dc.identifier.issn1434-1948-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/9393
dc.rightsDefault Licence-
dc.subjectbioinorganic chemistryen
dc.subjectcharge transferen
dc.subjectiodineen
dc.subjects ligandsen
dc.subjectnitrogen heterocyclesen
dc.subjectcharge-transfer complexesen
dc.subjectray crystal-structuresen
dc.subjectx-rayen
dc.subjectmolecular-interactionsen
dc.subjectantithyroid drugsen
dc.subjectiodothyronine deiodinaseen
dc.subjectiodine monobromideen
dc.subjectdiiodine adductsen
dc.subjectft-ramanen
dc.subjectmethimazoleen
dc.titleSynthesis and characterization of (PTU)I-2 (PTU=6-n-propyl-2-thiouracil) and (CMBZT)I-2 (CMBZT=5-chloro-2-mercaptobenzothiazole) and possible implications for the mechanism of action of anti-thyroid drugsen
heal.abstractDirect reaction of 6-n-propyl-2-thiouracil (PTU), a widely used anti-thyroid drug against hyperthyroidism (Graves' disease), or 5-chloro-2-mercaptobenzothiazole (CMBZTH) with iodine in a molar ratio of 1: 1 resulted in the formation of the charge-transfer (CT) complexes [(PTU)12] (1) or [(CMBZT)12] (2). All reactions were carried out in dichloromethane and water solutions. Compounds 1 and 2 were characterized by elemental analyses, FT-Raman, FT-IR, UV/Vis and H-1 NMR spectroscopy. The crystal structures of both complexes were determined by X-ray diffraction at 120(l) K (1) and 293(2) K (2). The charge-transfer nature of the bonds in the adducts 1 and 2 was verified by the lengthening of the I-I bond lengths as compared to the S-I bond lengths and by the characteristic CT bands observed in the UV spectra of the complexes. Compound 1 [(C7H10N2OS)I-2] [monoclinic with space group P2(1)/c and a = 9.8501(7), b = 10.3101(7), c = 12.0287(8) Angstrom, beta = 99.707(6)degrees, Z = 4] consists of a propylthiouracil ligand bonded with an iodine atom through sulfur. Extended intermolecular N-(HO)-O-... contacts link the molecules forming a supramolecular assembly. Compound 2 {(C7H4ClNS2)I-2} {orthorhombic, space group P2(1)2(1)2(1), a = 4.1650(10), b = 9.691(2), c = 28.471(6) Angstrom, Z = 41 consists of a 5-chloro-2-mercaptobenzothiazole ligand bonded with an iodine atom through sulfur. An extended intermolecular linkage via (IH)-H-...-N bonds leads to the formation of an extended structure. Attempts to draw conclusions on the behavior of a thioamide - when used as an anti-thyroidal drug - towards iodine have been made. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).en
heal.accesscampus-
heal.fullTextAvailabilityTRUE-
heal.identifier.secondary<Go to ISI>://000182708400023-
heal.journalNameEuropean Journal of Inorganic Chemistryen
heal.journalTypepeer reviewed-
heal.languageen-
heal.publicationDate2003-
heal.publisherWileyen
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.typejournalArticle-
heal.type.elΆρθρο Περιοδικούel
heal.type.enJournal articleen

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