Synthesis 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 diiodine
Φόρτωση...
Ημερομηνία
Τίτλος Εφημερίδας
Περιοδικό ISSN
Τίτλος τόμου
Εκδότης
Wiley-VCH Verlag
Περίληψη
Τύπος
Είδος δημοσίευσης σε συνέδριο
Είδος περιοδικού
peer reviewed
Είδος εκπαιδευτικού υλικού
Όνομα συνεδρίου
Όνομα περιοδικού
Chemistry-a European Journal
Όνομα βιβλίου
Σειρά βιβλίου
Έκδοση βιβλίου
Συμπληρωματικός/δευτερεύων τίτλος
Περιγραφή
Four 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.
Περιγραφή
Λέξεις-κλειδιά
bioinorganic chemistry, charge-transfer complexes, heterocyclic selenoamides, iodine adducts, selenium, i iodothyronine deiodinase, thyroid-hormone synthesis, ray crystal-structures, x-ray, transfer complexes, spectroscopic characterization, molecular adducts, selenium analog, ft-raman, iodine
Θεματική κατηγορία
Παραπομπή
Σύνδεσμος
<Go to ISI>://000240387000016
http://onlinelibrary.wiley.com/store/10.1002/chem.200501455/asset/6888_ftp.pdf?v=1&t=h0dvl0e1&s=bfc14010c226b3e464d5648e3dd769a9bcfff5a2
http://onlinelibrary.wiley.com/store/10.1002/chem.200501455/asset/6888_ftp.pdf?v=1&t=h0dvl0e1&s=bfc14010c226b3e464d5648e3dd769a9bcfff5a2
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