691904-24-2

Basic information

• Product Name: 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione
• Synonyms: 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione
• CAS NO: 691904-24-2
• Molecular Weight: 389.475
• Mol File: 691904-24-2.mol

Chemical Properties

• CAS DataBase Reference: 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione(691904-24-2)
• EPA Substance Registry System: 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione(691904-24-2)

Safety Data

• Hazardous Substances Data: 691904-24-2(Hazardous Substances Data)

Upstream product

• 38580-82-4 3-biphenylylmethyl chloride 
• 74772-78-4 5-(4-hydroxybenzyl)-2,4-thiazolidinedione 
• 588676-02-2 4-((3-bromobenzyl)oxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 15852-73-0 (3-Bromophenyl)methanol 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel thiazolidinediones as PPAR3/FFAR1 dual agonists

Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR3 is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR3 and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues.

RECEPTOR FUNCTION CONTROLLING AGENT

The GPR40 receptor function regulator of the present invention, which comprises a compound having an aromatic ring and a group capable of releasing cation is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.