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Interaction of Thioamides, Selenoamides and Amides with Di-iodine: A Study of the Mechanism of Action of Anti-thyroid Drugs

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Innovations in Chemical Biology

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This presentation is a brief review on the results of our work on iodine interaction with thioamides, selenoamides and amides. The thioamides, benzothia-zole-2-thione (BZT) (1), 6-n-propyl-2-thiouracil (PTU) (2), 5-chloro-2-mercap-tobenzothiazole (CMBZT) (3), N-methyl-benzothiazole-2-thione (NMBZT) (4), benzimidazole-2-thione (BZIM) (5), thiazolidine-2-thione (TZD) (6), 2-mercapto-pyridine (PYSH) (7), 2-mercapto-nicotinic acid (MNA) (8), 2-mercapto-benzoic acid (MBA) (9) and 2-mercapto-pyrimidine (PMT) (10) react with I2 producing three type of complexes of formulae: {[(HL)I2](I2)n } (HL= thioamide and n= 0, 1), {[(HL)2I+][I3 ȡ]} and {[(HL-L)]+[I3 −]}. The interaction of seleno-amides, derived from, 6- n-propyl-2-thiouracil (RSeU) (R= Me- (11), Et- (12), n-Pr- (13) and i-Pr- (14)) with I2, have also been studied and produced the complexes [(RSeU)I2] of “ spoke ” structure. These complexes are stable in non-polar solvents, but they decompose in polar solvents, producing dimeric diselenide compounds or undertake deselenation.

All these results are well correlated with the mechanism of action of anti-thyroid drugs.

Finally the amides pyridone-2-one (PYOH) (15) and 2-hydroxy-pyrimidine (PMOH 2 + Cl−) (16) react with I2 and produce the complexes {[(PYOH)3[(PYOH)]+∙I3 −}, {(PYOH) 6∙[(PYOH)2]2+∙ ((1/2)I−)∙((3/2)I7 −)∙(I2)} and {[PMOH2]+Cl−I2}. The structures of all these compounds are discussed.

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Authors and Affiliations

  1. Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, Ioannina, 45110, Greece

    Sotiris K. Hadjikakou & Nick Hadjiliadis

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  1. Sotiris K. Hadjikakou
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  2. Nick Hadjiliadis
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Correspondence to Nick Hadjiliadis .

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  1. Gazi University, Ankara, Turkey

    Bilge Şener

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Hadjikakou, S.K., Hadjiliadis, N. (2009). Interaction of Thioamides, Selenoamides and Amides with Di-iodine: A Study of the Mechanism of Action of Anti-thyroid Drugs. In: Şener, B. (eds) Innovations in Chemical Biology. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-6955-0_13

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