352469-17-1

Basic information

• Product Name: methyl 2-(4-hydroxy-3-iodophenyl)acetate
• Synonyms: methyl 2-(4-hydroxy-3-iodophenyl)acetate
• CAS NO: 352469-17-1
• Molecular Formula: C₉H₉IO₃
• Molecular Weight: 292.07043
• Mol File: 352469-17-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 2-(4-hydroxy-3-iodophenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(4-hydroxy-3-iodophenyl)acetate(352469-17-1)
• EPA Substance Registry System: methyl 2-(4-hydroxy-3-iodophenyl)acetate(352469-17-1)

Safety Data

• Hazardous Substances Data: 352469-17-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-(4-hydroxy-3-iodophenyl)acetate is used as an intermediate in the synthesis of 3-Iodothyroacetic Acid (I728600), a 3-Iodothyronamine metabolite. This metabolite has functional effects in FRTL-5 thyroid cells, which are crucial for understanding and potentially treating thyroid-related disorders. methyl 2-(4-hydroxy-3-iodophenyl)acetate's role in the synthesis process is essential for creating therapeutic agents that can target and modulate thyroid function.

Upstream product

• 14199-15-6 Methyl 4-hydroxyphenylacetate 

Downstream Products

• 140462-76-6 olopatadine hydrochloride 
• 1384866-65-2 (E)-methyl 4-{2-[4-(dimethylamino)but-1-enyl]benzyloxy}-3-iodophenylacetate 
• 878049-99-1 methyl 4-(p-triisopropylsilyloxy)phenoxy-3-iodophenyl acetate 
• 884320-55-2 methyl 2-[3-iodo-4-(4'-methoxymethoxyphenoxy)phenyl]acetate 
• 207451-22-7 methyl 4-allyloxy-3-iodophenyl acetate 
• 207451-24-9 4-allyloxy-3-iodophenyl acetic acid 
• 884320-56-3 2-[3-iodo-4-(4'-methoxymethoxyphenoxy)phenyl]acetaldehyde 
• 2229-49-4 4-(4-Hydroxy-phenoxy)-3-iod-phenethylalkohol 
• 878050-00-1 2-(3-iodo-4-(p-triisopropylsilyloxy)phenoxyphenyl)ethanol 

Relevant articles and documents

The discovery of tertiary-amine LXR agonists with potent cholesterol efflux activity in macrophages

The liver X receptors (LXR) play a key role in cholesterol homeostasis and lipid metabolism. SAR studies around tertiary-amine lead molecule 2, an LXR full agonist, revealed that steric and conformational changes to the acetic acid and propanolamine groups produce dramatic effects on agonist efficacy and potency. The new analogs possess good functional activity, demonstrating the ability to upregulate LXR target genes, as well as promote cholesterol efflux in macrophages.

Synthesis of [125I]-, [2H]-, and [ 3H]-labeled 3-iodothyronamine (T1AM)

3-Iodothyronamine (T1AM) is a novel metabolite of thyroid hormone. In HEK-293 cells expressing an orphan G-protein coupled receptor, the trace amine receptor, T1AM, potently increased cAMP accumulation. In mice, T1AM rapid

Trace amine-associated receptor agonists: Synthesis and evaluation of thyronamines and related analogues

We have previously shown that several thyronamines, decarboxylated and deiodinated metabolites of the thyroid hormone, potently activate an orphan G protein-coupled receptor in vitro (TAAR1) and induced hypothermia in vivo on a rapid time scale [Scanlan, T. S.; Suchland, K. L.; Hart, M. E.; Chiellini, G.; Huang, Y.; Kruzich, P. J.; Frascarelli, S.; Crossley, D. A.; Bunzow, J. R.; Ronca-Testoni, S.; Lin, E. T.; Hatton, D.; Zucchi, R.; Grandy, D. K. 3-Iodothyronamine is an endogenous and rapid-acting derivative of thyroid hormone. Nat. Med. 2004, 10 (6), 638-642]. Herein, we report the synthesis of these thyronamines. Additionally, a large number of thyroamine derivatives were synthesized in an effort to understand the molecular basis of TAAR1 activation and hypothermia induction. Several derivatives were found to potently activate both rTAAR1 and mTAAR1 in vitro (compounds 77, 85, 91, and 92). When administered to mice at a 50 mg/kg dose, these derivatives all induced significant hypothermia within 60 min and exhibited a hypothermic induction profile analogous to 3-iodothyronamine (1, T1AM) except 91, which proved to be more efficacious. On the basis of this result, a dose-dependent profile for 91 was generated and an ED50 of 30 μmol/kg was calculated. Compound 91 proved to be more potent than T1AM for TAAR1 activation and exhibits increased potency and efficacy for hypothermia induction. These data further strengthen the pharmacological correlation linking TAAR1 activation by thyronamines and hypothermia induction in mice.

SmI2-mediated sequential radical cyclization/anionic capture of aryl iodides on solid support

Aryl radicals were generated by SmI2 on solid support, cyclized on to C=C bond, and reduced to their organosamarium anionic species followed by electrophilic capture. However, the capture reaction was substrate-dependant in solution and on soli