805250-24-2

Basic information

• Product Name: Benzenemethanol, 3-benzo[b]thien-5-yl-
• CAS NO: 805250-24-2
• Molecular Formula: C15H12OS
• Molecular Weight: 240.326
• Mol File: 805250-24-2.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, 3-benzo[b]thien-5-yl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 3-benzo[b]thien-5-yl-(805250-24-2)
• EPA Substance Registry System: Benzenemethanol, 3-benzo[b]thien-5-yl-(805250-24-2)

Safety Data

• Hazardous Substances Data: 805250-24-2(Hazardous Substances Data)

Upstream product

• 805250-23-1 3-(1-benzothiophen-5-yl)benzaldehyde 
• 4923-87-9 5-bromobenzo[b]thiophene 
• 87199-16-4 3-Formylphenylboronic 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.

ALKOXYPHENYLPROPANOIC ACID DERIVATIVES

The present invention aims at provision of a novel compound having a GPR40 receptor function modulating action, which is useful as an insulin secretagogue, an agent for the prophylaxis or treatment of diabetes and the like. The compound represented by the formula: wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonistic activity and superior properties as pharmaceutical products such as stability and the like, and can be safe and useful pharmaceutical agents as agents for the prophylaxis or treatment of GPR40 receptor-related pathology or diseases in mammals.