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
Φόρτωση...
Ημερομηνία
Συγγραφείς
Antoniadis, C. D.
Corban, G. J.
Hadjikakou, S. K.
Hadjiliadis, N.
Kubicki, M.
Warner, S.
Butler, I. S.
Τίτλος Εφημερίδας
Περιοδικό ISSN
Τίτλος τόμου
Εκδότης
Wiley
Περίληψη
Τύπος
Είδος δημοσίευσης σε συνέδριο
Είδος περιοδικού
peer reviewed
Είδος εκπαιδευτικού υλικού
Όνομα συνεδρίου
Όνομα περιοδικού
European Journal of Inorganic Chemistry
Όνομα βιβλίου
Σειρά βιβλίου
Έκδοση βιβλίου
Συμπληρωματικός/δευτερεύων τίτλος
Περιγραφή
Direct 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).
Περιγραφή
Λέξεις-κλειδιά
bioinorganic chemistry, charge transfer, iodine, s ligands, nitrogen heterocycles, charge-transfer complexes, ray crystal-structures, x-ray, molecular-interactions, antithyroid drugs, iodothyronine deiodinase, iodine monobromide, diiodine adducts, ft-raman, methimazole
Θεματική κατηγορία
Παραπομπή
Σύνδεσμος
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Γλώσσα
en
Εκδίδον τμήμα/τομέας
Όνομα επιβλέποντος
Εξεταστική επιτροπή
Γενική Περιγραφή / Σχόλια
Ίδρυμα και Σχολή/Τμήμα του υποβάλλοντος
Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας