85828-82-6

Basic information

• Product Name: ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate
• Synonyms: ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate;3,5-Diiodo-4-(4-methoxyphenoxy)benzeneacetic acid ethyl ester;Einecs 288-610-5;3,5-Diiodo-4'-O-Methyl Thyroacetic Acid Ethyl Ester;Levothyroxine Sodium Impurity 8;3,5-Diiodo-4a€-O-methyl Thyroacetic Acid Ethyl Ester
• CAS NO: 85828-82-6
• Molecular Formula: C₁₇H₁₆I₂O₄
• Molecular Weight: 538.11548
• EINECS: 288-610-5
• Product Categories: Aromatics, Drug Analogues, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 85828-82-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 479.5°Cat760mmHg
• Flash Point: 243.8°C
• Appearance: /
• Density: 1.808g/cm³
• Vapor Pressure: 2.35E-09mmHg at 25°C
• Refractive Index: 1.629
• Solubility: Dichloromethane
• CAS DataBase Reference: ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate(85828-82-6)
• EPA Substance Registry System: ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate(85828-82-6)

Safety Data

• Hazardous Substances Data: 85828-82-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

3,5-Diiodo-4’-O-methyl Thyroacetic Acid Ethyl Ester is a derivative of 3,5-Diiodo Thyroacetic Acid (D455140), the acetic acid analog of Thyroxine (T425601). It is a reactant in the preparation of bifunctional thyrointegrin inhibitors, thyroxine (T425601) and triiodothyronine (T795380).

InChI:InChI=1/C17H16I2O4/c1-3-22-16(20)10-11-8-14(18)17(15(19)9-11)23-13-6-4-12(21-2)5-7-13/h4-9H,3,10H2,1-2H3

Upstream product

• 156-38-7 4-hydroxyphenylacetate 
• 861065-72-7 [4-(4-methoxy-phenoxy)-3,5-dinitro-phenyl]-acetic acid ethyl ester 
• 83799-60-4 (4-hydroxy-3,5-dinitro-phenyl)-acetic acid ethyl ester 
• 101588-11-8 C₁₇H₂₀N₂O₄ 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 1300559-71-0 methyl {4-[4-(2-chloroethoxy)-3,5-diiodophenoxy]-3,5-diiodophenyl}-acetate 
• 1300559-73-2 Lithium [4-(4-{2-[(diaminomethylene)amino]ethoxy}-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate 
• 1300559-75-4 (4-{4-[2-(carbamoylamino)ethoxy]-3,5-diiodophenoxy}-3,5-diiodophenyl)acetic acid 
• 1300559-77-6 {4-[4-(3-aminopropoxy)-3,5-diiodophenoxy]-3,5-diiodophenyl}acetic acid 
• 1300857-63-9 C₁₈H₁₇I₄NO₄ 
• 1300559-73-2 lithium [4-(4-{2-[(diaminomethylene)amino]-ethoxy}-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate 
• 51-24-1 3,3',5-triiodothyroacetic acid 
• 67-30-1 tetrac 
• 92436-93-6 2-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)acetic acid 

Relevant articles and documents

Synthesis of new analogs of tetraiodothyroacetic acid (tetrac) as novel angiogenesis inhibitors for treatment of cancer

In the angiogenesis process, integrins, which are members of a family of cell surface transmembrane receptors, play a critical role particularly in blood vessel formation and the local release of vascular growth factors. Thyroid hormones such as L-thyroxine (T4) and 3,5,3′-triiodo-L-thyronine (T3) promote angiogenesis and tumor cell proliferation via integrin αvβ3 receptor. At or near an arginine-glycine-aspartate (RGD) recognition site on the binding pocket of integrin αvβ3, tetraiodothyroacetic acid (tetrac, a deaminated derivative of T4) is a thyrointegrin receptor antagonist and blocks the actions of T3 and T4 as well as different growth factors-mediated angiogenesis. In this study, we synthesized novel tetrac analogs by modifying the phenolic moiety of tetrac and tested them for their anti-angiogenesis activity using a Matrigel plug model for angiogenesis in mice. Pharmacological activity results showed that tetrac can accommodate numerous modifications and maintain its anti-angiogenesis activity.

Design, synthesis, and biological evaluation of bifunctional thyrointegrin inhibitors: New anti-angiogenesis analogs

Context: Inhibition of pathological angiogenesis. Objective: Obtaining new transactivator, bifunctional, thyroid antagonist, non-toxic anti-angiogenic compounds. Materials and methods: In silico drug design, synthesis in bulk and biological evaluation in chick chorioallantoic membrane (CAM) model. Results: Significant inhibition (range 6573%) at 0.252.0 g/ml doses. Discussion and conclusion: The synthesis of compounds (9), (10), and (11) incorporating long-chain moieties guanidine, urea, methyl amine and, propyl amine substitutions, respectively, into the core molecular framework of tetrac (tetraiodothyroacetic acid) were undertaken. The evaluation of the anti-angiogenic bioactivity of these compounds in the CAM model revealed no loss of activity in comparison with tetrac and XT199, which showed nearly 86% inhibition at dose levels of 1 and 0.5 g/ml, respectively, and validated the concept.