805250-48-0

Basic information

• Product Name: [1,1'-Biphenyl]-3-carboxaldehyde, 2',6'-dimethyl-4'-(phenylmethoxy)-
• CAS NO: 805250-48-0
• Molecular Formula: C22H20O2
• Molecular Weight: 316.4
• Mol File: 805250-48-0.mol

Chemical Properties

• CAS DataBase Reference: [1,1'-Biphenyl]-3-carboxaldehyde, 2',6'-dimethyl-4'-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-3-carboxaldehyde, 2',6'-dimethyl-4'-(phenylmethoxy)-(805250-48-0)
• EPA Substance Registry System: [1,1'-Biphenyl]-3-carboxaldehyde, 2',6'-dimethyl-4'-(phenylmethoxy)-(805250-48-0)

Safety Data

• Hazardous Substances Data: 805250-48-0(Hazardous Substances Data)

Upstream product

• 805250-31-1 4’-hydroxy-2’,6’-dimethyl-3-biphenylcarbaldehyde 
• 100-39-0 benzyl bromide 
• 87199-16-4 3-Formylphenylboronic acid 
• 7463-51-6 4-bromo-3,5-dimethylphenol 

Downstream Products

• 805249-07-4 methyl (6-{[4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2,3-dihydro-1-benzofuran-3-yl)acetate 
• 805250-49-1 [4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-yl]methanol 
• 805249-08-5 (6-{[4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2,3-dihydro-1-benzofuran-3-yl)acetic acid 

Relevant articles and documents

Identification of fused-ring alkanoic acids with improved pharmacokinetic profiles that Act as G protein-coupled receptor 40/free fatty acid receptor 1 agonists

The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl} propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to β-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy} -2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

AMINOPHENYLPROPANOIC ACID DERIVATIVE

A compound represented by the formula (1): wherein each symbol is as defined in the specification, and a salt thereof and a prodrug thereof unexpectedly have superior GPR40 receptor agonist activity, superior in the properties as a pharmaceutical product such as stability and the like, and can be a safe and useful pharmaceutical agent as a drug for the prophylaxis or treatment of GPR40 receptor related pathology or diseases such as diabetes and the like.