Synthesis of Analogues of 2-iodohexadecanal, a Regulator of Iodine Metabolism in the Thyroid Gland

Abstract

Com o objetivo futuro de fazer um estudo da relação estrutura-atividade, foram sintetisados vários derivados do 2-iodo-hexadecanal [1], um regulador do metabolismo de iodo na glândula tireóide, que diferem no comprimento da cadeia, natureza do substituinte e grupo funcional terminal.With the object of performing a structure-activity relationship study, we have synthesized several analogues of 2-iodohexadecanal [1], a regulator of iodine metabolism in the thyroid gland, differing by the chain length, the nature of the substituent, and/or the terminal functional group.

Metabolism of Myeloperoxidase-derived 2-Chlorohexadecanal

“…The results herein demonstrate that both endothelial cells and neutrophils oxidize and reduce 2-ClHDA to its respective chlorinated fatty acid and chlorinated fatty alcohol, which are subsequently incorporated into complex glycerolipids. 16:0 FA were subjected to ␣-chlorination with chlorine(g) using the Hell-VolhardZelinsky reaction and phosphorous as the catalyst (40). Briefly, 16:0 FA was melted at 80°C before an equimolar amount of phosphorous trichloride in dichloromethane was added to the reaction vial.…”

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

“…For α-iodo fatty acids 7 , two different routes were evaluated. Iodinated fatty acids 7e , f were prepared via reaction of the corresponding fatty acids 4e , f with iodine and chlorosulfonic acid [ 28 ]. However, this transformation was not quantitative as it resulted in a mixture of both iodinated and non-iodinated fatty acids.…”

“…As described in [ 28 ] fatty acid 4e or 4f (1.56 mmol), iodine (0.5 equiv, 0.20 g, 0.78 mmol) and chlorosulfonic acid (1 equiv, 0.1 mL, 1.56 mmol) were dissolved in 1.6 mL of dry 1,2-dichloroethane. The reaction mixture was heated at 80 °C for 5 h, after which it was diluted with 3 mL 1,2-dichloroethane and washed successively with water (2 × 5 mL) and an aqueous 0.1 M Na 2 S 2 O 3 solution until the color changed from pink to white.…”

Naturally occurring organoiodines

“…As no formation of 2-iodohexadecanoic acid could be detected, the reduction into the biologically inactive 2-IHDO ( 173) was determined to be a major metabolic pathway of 2-IHDA (172) in dog thyrocytes. 189 (2R)-(+)-and (2S)-(À)-2-IHDA (172) were synthesised 190 in ve steps and 62% overall yield from chiral enol ethers via the iodocyclisation and chromatographic separation of the resulting diastereomeric 1 0 -iododioxanes. The absolute congurations were assigned through chemical correlation and by application of Mosher's method to the esters obtained by methanolysis of (2R)-and (2S)-2-IHDA followed by derivatisation.…”