Antithyroid Drug Analogues Synthesis and Structural Study

Nath, Ipsita and G, Prabusankar (2014) Antithyroid Drug Analogues Synthesis and Structural Study. Masters thesis, Indian Institute of Technology, Hyderabad.

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Abstract

Thiourea-based Antithyroid drugs propylthiouracil (PTU), methimazole (MMI), and carbimazole (CBZ) may block the thyroid hormone biosynthesis whereas selenourea containing drugs reduce H2O2, which is required for oxidation of catalyst leads to decrease in thyroid hormone production. Thus, new tris organo selone derivatives 3,3',3''-((2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene))tris(1-(2,6-alkyl/aryl)-1H-imidazole-2(3H)-selenone) 4a-4f have been synthesized for the first time by the reaction of 1,1',1''-((2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene))tris(3-alkyl/aryl-1H-imidazol-3-ium)bromide (1eq.), potassium carbonate (6eq.) and selenium powder (6eq.). These new molecules have been characterized by multinuclear NMR (1H NMR, 13C NMR, DEPT), FT-IR and UV-vis. studies. The 1H and 13C chemical shifts have been confirmed on the basis of correlation spectra e.g HSQC, HMBC. Photophysical properties have been derived from UV−vis. The molecular structures of 4a, 4b, 4c, 4d and 4e have been determined by X-ray crystallography, which suggests that these compounds exist as zwitterions in which the selenium atom carries a large negative charge which enhances the nucleophilic activity of compounds

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