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Interactions of Antithyroid Drugs and Their Analogues with Halogens and their Biological Implications

Roy, Gouriprasanna and Bhabak, Krishna P and Mugesh, Govindasamy (2011) Interactions of Antithyroid Drugs and Their Analogues with Halogens and their Biological Implications. In: Crystal Growth & Design, 11 (6). pp. 2279-2286.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/cg101688v


The selenium analogue of antithyroid drug methimazole (MSeI) reacts with molecular bromine to produce two different types of novel complexes depending upon the molar ratio of MSeI to Br-2 in the reaction medium: Dicationic diselenide complex with two Br- ions as counterions is produced in the reaction of MSeI with 0.5 equiv of Br-2 (MSeI/Br-2, 1.0:0.5), whereas a stable 10-Se-3 hypervalent ``T-shaped'' complex featuring a linear Br-Se-Br moiety was produced when MSeI was treated with Br-2 in an equimolar ratio (MSeI/Br-2, 1.0:1.0). A substitution at the free N-H group in MSeI alters its reactivity toward iodine/bromine. For example, the N,N-disubstituted selones exclusively produce the corresponding 10-Se-3 hypervalent ``T-shaped'' complexes in the reaction with I-2. In the presence of the lectoperoxidase/H2O2/I- system, N,N-dimethylimidazole-2-selone produces the corresponding dicationic diselenide with two I- counterions as the final metabolite. The formation of ionic species in these reactions is confirmed by single crystal X-ray diffraction studies and in some cases by Fourier transform-Raman spectroscopic investigations.

Item Type: Journal Article
Publication: Crystal Growth & Design
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 22 Jun 2011 09:48
Last Modified: 22 Jun 2011 09:48
URI: http://eprints.iisc.ac.in/id/eprint/38435

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