534-51-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DIIODO-DL-THYRONINE is used as a potential therapeutic agent for the treatment of obesity due to its capacity to regulate energy metabolism and improve lipid metabolism, thereby contributing to weight reduction.
Used in Metabolic Syndrome Treatment:
In the field of endocrinology, 3,5-DIIODO-DL-THYRONINE is considered for its potential role in managing metabolic syndrome, as it may help in addressing the underlying metabolic imbalances associated with the condition.
Used in Research and Development:
3,5-DIIODO-DL-THYRONINE serves as a valuable compound in scientific research, particularly in studies focused on understanding the mechanisms of thyroid hormone action and their implications in various physiological processes and disease states.

Upstream product

• 2944-48-1 2-tert-butylanisole 
• 2444-19-1 4-hydroxyphenyl benzoate 
• 54337-43-8 1-oxaspiro[2.5]octa-4,7-dien-6-one 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 1016161-91-3 C₃₀H₄₃I₂NO₆Si 
• 1431868-05-1 C₂₁H₂₃I₂NO₆ 
• 178877-78-6 C₂₀H₂₁I₂NO₆ 
• 51-48-9 L-thyroxine 
• 21959-36-4 N-acetyl-3,5-diiodo-L-tyrosine ethyl ester 
• 1027-28-7 N-acetyl-3,5-diiodo-L-tyrosine 
• 83249-56-3 N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester 
• 19231-06-2 4,4'-dimethoxy-diphenyliodonium bromide 
• 94345-95-6 2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid 
• 49553-16-4 {Cu(HOC₆H₂I₂CH₂CH(NH₂)COO)2} 

Downstream Products

• 94298-44-9 N-formyl-3,5-diiodo-DL-thyronine 
• 3687-09-0 3,5-Diiodothyronamine 
• 51-48-9 L-thyroxine 
• 1041-01-6 3,5-diiodo-L-thyronine 
• 5563-89-3 D-Diiodothyronine 
• 51-49-0 dextrothyroxine 
• 94298-44-9 N-formyl-3,5-diiodo-L-thyronine 
• 120408-14-2 N-formyl-3,5-diiodo-D-thyronine 
• 93326-20-6 3,5-Dicyan-DL-thyronin 
• 809-70-1 N-Trifluoracetyl-3-<4-(4-hydroxy-phenoxy)-3,5-dicyan-phenyl>-DL-alanin-ethylester 
• 2389-85-7 3,5-diiodo-4-(4-methoxy-phenoxy)-trans-cinnamic acid 
• 49553-20-0 {Cu(HOC₆H₄OC₆H₂I₂CH₂CH(NH₂)COO)2} 
• 63238-71-1 2,2,3,3,4,4,4-Heptafluoro-butyric acid 4-{4-[2-(2,2,3,3,4,4,4-heptafluoro-butyrylamino)-2-methoxycarbonyl-ethyl]-2,6-diiodo-phenoxy}-phenyl ester 
• 1549-09-3 N-Trifluoracetyl-3,5-diiod-DL-thyronin-ethylester 

Relevant academic research and scientific papers

Preparation method of levothyroxine sodium

The invention belongs to the field of pharmaceutical synthesis, and discloses a preparation method of levothyroxine sodium. The preparation method comprises the following steps: (1) taking 3,5-diiodo-L-tyrosine as a raw material, and preparing N-acetyl-L-tyrosine by firstly introducing acetyl protection to an amino group; (2) then preparing N-acetyl-3,5-diiodo-L-tyrosine ethyl ester under the action of thionyl chloride; (3) preparing N-acetyl-O-(4-methyoxyphenyl)-3,3-diiodo-L-tyrosine ethyl ester by carrying out Chan-Lam reaction through copper catalysis; (4) removing a protective group undera strong acidity condition, thus obtaining O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine; (5) then reacting with iodine, and preparing O-(4-hydroxy-3,5-diiodo phenyl)-3,5-diiodo-L-tyrosine disodium salt under the action of sodium hydroxide; (6) finally, regulating pH (Potential of Hydrogen) through glacial acetic acid, thus obtaining the levothyroxine sodium. According to the preparation method disclosed by the invention, the key Chan-Lam reaction and other reaction steps are optimized, so that the reaction time can be greatly shortened, and the reaction yield can be increased; the preparation method is simple in technology, convenient to operate and suitable for industrial production.

Improved method for synthesizing L-thyroxine sodium

The invention relates to an improved method for synthesizing L-thyroxine sodium. The improved method includes the steps that 3,5-diiodomethane-L-tyrosine is used as a raw material, and then subjectedto a copper complex reaction, a coupling reaction, an acid hydrolysis reaction, an iodine generation reaction and a salt forming reaction to obtained the L-thyroxine sodium. According to the improvedmethod for synthesizing the L-thyroxine sodium, the yield of the L-thyroxine sodium can be improved, the product cost is lowered, and industrialization is convenient.

Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.

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.

PHARMACEUTICAL COMPOSITIONS COMPRISING DIIODOTHYRONINE AND THEIR THERAPEUTIC USE

The present invention relates to a pharmaceutical composition comprising, as active substance, at least one hormone chosen among 3,5-diiodothyronine (3,5-T2), 3′,3-diiodothyronine (3′,3-T2), 3′,5-diiodothyronine (3′,5-T2), 3′-iodothyronine (3′-T), 3-iodothyronine (3-T) or 5-iodothyronine (5-T), in association with a pharmaceutically acceptable vehicle.

A concise synthesis of thyroxine (T4) and 3,5,3'-Triiodo-L-thyronine (T3)

The mono- and di-iodo derivatives of 1-oxaspiro[2,5]bicycloocta-4,7-dien-6-one, 8 and 9, reacted readily with 3,5-diiodo-L-tyrosine at pH 8.0 to give 3,5,3'-triiodo-L-thyronine (T3) and thyroxine in 70% and 94% yields respectively. In turn, 8 and 9 were prepared by the sodium bismuthate oxidation of their corresponding iodinated p-hydroxybenzyl alcohol derivatives, 6 and 7 in 32% and 37% yields.