58491-25-1

Upstream product

• 25112-94-1 (6-methoxy-3,4-dihydro-2H-[1]naphthyliden)-acetic acid ethyl ester 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 68254-80-8 6'-methoxy-1',2',3',4'-tetrahydro-1'-naphthylacetic acid 
• 805248-47-9 C₂₉H₃₂O₃ 
• 805248-48-0 {6-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1,2,3,4-tetrahydronaphthalen-1-yl}acetic acid 
• 58491-26-2 6-hydroxy-7-benzoyl-1,2,3,4-tetrahydro-1-naphthylacetic acid ethyl ester 

Relevant academic research and scientific papers

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.

GPR120 RECEPTOR AGONISTS AND USES THEREOF

GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

Synthesis of novel molecular probes inspired by harringtonolide

A novel harringtonolide-inspired scaffold containing a cycloheptatriene ring and two fused cyclopentane rings has been synthesised from simple starting materials. The scaffold, containing a similar substitution pattern and relative stereochemistry to the

ARYL GPR120 RECEPTOR AGONISTS AND USES THEREOF

Aryl GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

GPR120 RECEPTOR AGONISTS AND USES THEREOF

GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

A multireceptorial binding reinvestigation on an extended class of σ ligands: N-[ω-(indan-1-yl and tetralin-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine reveal high affinities towards σ1 and EBP sites

New 1-[ω-(2,3-dihydro-1H-inden-1-yl)- and (2,3-dihydro-5-methoxy-1H-inden-1-yl)alkyl]- and 1-[ω-(1,2,3,4-tetrahydronaphthalen-1-yl)- and (6-methoxy- or 6-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine were synthesized, as homologous compounds of an existing series of σ ligands, in order to carry out σ receptor subtypes structure-affinity relationships. The new compounds and some of their related analogues, already reported, were tested in new multireceptorial radioligand binding assays. As reference compounds, the known σ1 ligands SA 4503, BD 1008 and NE 100 were also prepared and tested. All reported compounds showed high σ1 affinity assayed by (+)-[3H]-pentazocine on guinea-pig brain (apparent Ki=1.75-72.2 nM) and moderate or low σ2 affinity by [3H]-DTG on rat liver, in contrast with previous results. One tertiary amine function spaced by a five-membered chain from a phenyl group is the structural feature shared by the most active compounds 26 and 43 and some reference σ1 ligands. The reported σ1 ligands, including reference compounds, also demonstrated a high affinity towards EBP (Δ8-Δ7 sterol isomerase) site (apparent Ki=0.48-14.8 nM) and some of them (37 and 44) were good ligands at L-type Ca++ channel. 1-[4-(2,3-Dihydro-1H-inden-1-yl)butyl]-3,3-dimethylpiperidine (26) was the best mixed σ1 and EBP ligand (apparent Ki=1.75 and 1.54 nM, respectively) with a good selectivity versus σ2 receptor (138- and 157-fold, respectively).