1016161-91-3

Upstream product

• 128781-80-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3,5-diiodophenyl)propanoate 
• 643090-93-1 (4-((triisopropylsilyl)oxy)phenyl)boronic acid 
• 60-18-4 L-tyrosine 
• 1080-06-4 L-Tyr-OMe 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 

Downstream Products

• 88404-22-2 (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4-hydroxy-3,5-diaiodophenoxy)-3,5-diaiodophenyl)propanoic acid 
• 51-48-9 L-thyroxine 
• 1431868-05-1 C₂₁H₂₃I₂NO₆ 
• 178877-78-6 C₂₀H₂₁I₂NO₆ 
• 1041-01-6 3,5-diiodo-L-thyronine 

Relevant academic research and scientific papers

The synthesis of 13C9-15N-labeled 3,5-diiodothyronine and thyroxine

Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9- 15N-T2 and 13C9-15N- T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Characterization of thyroid hormone receptor α (TRα)-specific analogs with varying inner- and outer-ring substituents

Analogs of the TRα-specific thyromimetic CO23 were synthesized and analyzed in vitro using competitive binding and transactivation assays. Like CO23, all analogs bind to both thyroid hormone receptor subtypes with about the same affinity; however, modification of CO23 by derivatization of the 3′ position of the outer-ring or replacement of the inner-ring iodides with bromides attenuates binding. Despite lacking a preference in binding to TRα, all analogs display TRα-specificity in transactivation assays using U2OS and HeLa cells. At best, several agonists exhibit an approximately 6-12-fold preference in transactivation when tested with TRα in HeLa cells. One analog, CO24, showed in vivo TRα-specific action in a tadpole metamorphosis assay.