211110-63-3

Usage

Uses

GC 1 is a high affinity thyroid receptor α (TRα) and TRβ agonist.

Biological Activity

sobetirome (3,5-dimethyl-4[(4'-hydroxy-3'-isopropylbenzyl)-phenoxy] acetic acid, also known as gc-1 and qrx-431, is a member of a class of compounds known as selective thyromimetics.it was firstly developed by thomas scanlan’s group at the university of california-san francisco (ucsf) in 1995 1.in cholesterol-fed rats, sobetirome was shown to lower plasma cholesterol in a dose-dependent manner by up to 75% of untreated controls. in hypercholesterolemic mice, sobetirome was failed to induce ldl receptor mrna expression. in different mouse models, sobetirome and t-0681 were shown to promote bile acid production and biliary sterol secretion. in cynomolgus monkeys, sobetirome was shown to reduce plasma cholesterol in a dose-dependent manner by up to 30%. both sobetirome and t-0681 were shown to increase hepatic expression of the hdl receptor (scavenger receptor-bi, sr-bi) in animals.in phase i

Biochem/physiol Actions

Sobetirome is also termed as 2-(4-(4-(benzyloxy)-3-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid/ GC-1. It has an inner-ring and negatively charged carboxylate groups at physiological pH. Sobetirome is considered as a cholesterol lowering agent in humans.

references

1. tancevski i, demetz e, eller p. sobetirome: a selective thyromimetic for the treatment of dyslipidemia. recent pat cardiovasc drug discov. 2011 jan;6(1):16-9.

InChI:InChI=1/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)

Upstream product

• 328236-48-2 [3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzyl)phenoxy]tert-butylacetate 
• 807380-39-8 [3,5-dimethyl-4-(3'-isopropyl-4'-nitroveratrylbenzyl)phenoxy]acetate 
• 7463-51-6 4-bromo-3,5-dimethylphenol 
• 26307-50-6 4-bromo-2-isopropyl-phenol 
• 328236-42-6 4-bromo-2-isopropyl phenyl methoxymethyl ether 
• 328236-44-8 2,6-dimethyl-4-(triisopropyl-silanyloxy)-benzaldehyde 
• 328236-43-7 (4-bromo-3,5-dimethylphenoxy)triisopropylsilane 
• 328236-47-1 3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzyl)phenol 
• 328236-46-0 3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzyl)-O-triisopropylsilylphenol 
• 328236-45-9 3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzylhydroxy)-O-triisopropylsilylphenol 
• 169247-38-5 1-benzyloxy-4-bromo-2-isopropylbenzene 
• 904925-63-9 (4-benzyloxy-3-isopropyl-phenyl)-(2,6-dimethyl-4-triisopropylsilanyloxy-phenyl)-methanol 
• 5437-45-6 Benzyl bromoacetate 
• 88-69-7 2-(1-methylethyl)phenol 

Relevant academic research and scientific papers

Liver-targeting compound with thyroid hormone receptor stimulating agent characteristics and pharmaceutical composition of liver targeting compound

The invention belongs to the field of biomedicines, particularly relates to the field of targeting drugs and more specifically relates to a liver-targeting compound with thyroid hormone receptor stimulating agent characteristics and a pharmaceutical compo

Novel Phosphinic Acid-Containing Thyromimetics

The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.

Photo-caged agonists of the nuclear receptors RARγ and TRβ provide unique time-dependent gene expression profiles for light-activated gene patterning

Light-activated gene expression systems hold promise as new tools for studying spatial and temporal gene patterning in multicellular systems. Photo-caged forms of nuclear receptor agonists have recently been shown to mediate photo-dependent transcription in mammalian cells, however, because intracellularly released agonists can rapidly diffuse out of cells, the photo-initiated transcription response is only transient and limited to only a few hours in reported examples. Herein we describe a photo-caged thyroid hormone receptor agonist that provides a robust 36 h transcription response to a single irradiation event. These findings are in contrast to a closely related system, which uses a caged retinoic acid receptor agonist, which provides only a short transcription response. Comparison of the two systems, show that the duration of transcription response is not controlled by the rate of diffusion of free ligand out of the cell, but perhaps by the duration of ligand-induced transcription/stability of the active transcription complex.

Improved synthesis of the iodine-free thyromimetic GC-1

Synthesis of the TRβ-selective thyromimetic GC-1 has been improved using methoxymethyl (MOM) and triisopropylsilyl (TiPS) substituents as phenolic protecting groups. The new synthetic route is adaptable to analogue design. (C) 2000 Elsevier Science Ltd.