456-84-8

Upstream product

• 19231-06-2 4,4'-dimethoxy-diphenyliodonium bromide 
• 111088-56-3 3,5-diiodo-O-methyl-N-(trifluoroacetyl)-L-thyronine methyl ester 
• 203585-45-9 3,5-diiodo-L-thyronine methyl ester 
• 407-25-0 trifluoroacetic anhydride 
• 1041-01-6 3,5-diiodo-L-thyronine 
• 100-66-3 methoxybenzene 

Downstream Products

• 111087-72-0 3-[4-(3-Allyl-4-hydroxy-phenoxy)-3,5-diiodo-phenyl]-2-amino-propionic acid 
• 111088-24-5 3,5-diiodo-O-prop-2-enyl-N-(trifluoroacetyl)-L-thyronine methyl ester 
• 482-09-7 3,5-diiodo-O'-(tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-L-thyronine-methyl ester 

Relevant academic research and scientific papers

Thyroid Hormone Analogues. Synthesis of 3'-Substituted 3,5-Diiodo-L-thyronines and Quantitative Structure-Activity Studies of in Vivo Thyromimetic Activities in Rat Liver and Heart

Twenty-nine 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by new route involving manipulation of a 3'-formyl intermediate.In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines.Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accomodate a phenyl or cyclohexyl group.Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the ajacent 4'-hydroxyl.The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar.However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences.A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar reactivity) is included in the analysis.These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

Pyridyl and pyridazinyl substituted thyronine compounds having selective thyromimetic activity

This invention relates to chemical compounds which have selective thyromimetic activity. A compound of this invention is 3,5-dibromo-3''-[6-oxo-3(1H)-pyridazinylmethyl]-thyronine.