691905-26-7

Usage

Uses

Used in Perfume and Fragrance Industry:
3-(2,6-Dimethylphenyl)benzaldehyde is used as a flavoring and fragrance agent for its strong, aromatic scent. It is commonly incorporated into various cosmetic and personal care products to provide a pleasant and lasting aroma.
Used in Organic Synthesis:
3-(2,6-Dimethylphenyl)benzaldehyde serves as a precursor in organic synthesis, allowing for the creation of a wide range of chemical compounds. Its unique structure makes it a versatile building block in the development of new molecules.
Used in Chemical Reactions:
As a reagent, 3-(2,6-Dimethylphenyl)benzaldehyde is utilized in various chemical reactions to facilitate the synthesis of different compounds. Its participation in these reactions contributes to the advancement of chemical research and the production of new materials.

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 100379-00-8 2,6-dimethylbenzene boronic acid 
• 576-22-7 2-Bromo-m-xylene 
• 87199-16-4 3-Formylphenylboronic acid 

Downstream Products

• 691905-27-8 (2',6'-dimethyl-[1,1'-biphenyl]-3-yl)methanol 
• 1218910-02-1 C₁₆H₁₉N 
• 955929-56-3 2',6'-dimethyl-[1,1'-biphenyl]-3-carboxylic acid 
• 1620080-47-8 methyl 2-(2',6'-dimethylbiphenyl-3-yl)benzo[d]oxazole-5-carboxylate 
• 1620080-49-0 (2-(2',6'-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methanol 
• 1390641-89-0 3-(4-(((2',6'-dimethyl-[1,1'-biphenyl]-3-yl)methyl)amino)-2-fluorophenyl)propanoic acid 
• 805249-15-4 {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indole-1-yl}acetic acid 
• 805250-53-7 5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indole 
• 1359668-80-6 {2-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl}acetic acid 

Relevant academic research and scientific papers

SULFINIC ACID COMPOUNDS AS FREE FATTY ACID RECEPTOR AGONISTS

The present invention relates to certain compounds, their use in therapy, as well as to pharmaceutical compositions including said compounds. Specifically, the invention relates to certain compounds and pharmaceutical compositions including these compounds for the treatment of metabolic disorders including, for example, diabetes, obesity, metabolic syndrome, fatty liver disease, and bone disorders.

Design, synthesis and structure–activity relationship studies of novel free fatty acid receptor 1 agonists bearing amide linker

The free fatty acid receptor 1 (FFA1/GPR40) has attracted extensive attention as a novel antidiabetic target. Aiming to explore the chemical space of FFA1 agonists, a new series of lead compounds with amide linker were designed and synthesized by combining the scaffolds of NIH screened lead compound 1 and GW9508. Among them, the optimal lead compound 17 exhibited a considerable agonistic activity (45.78%) compared to the NIH screened compound 1 (15.32%). During OGTT in normal mice, the compound 17 revealed a significant glucose-lowering effect (?23.7%) at the dose of 50?mg/kg, proximity to the hypoglycemic effect (?27.8%) of Metformin (200?mg/kg). In addition, the compound 17 (100?mg/kg) also exhibited a significant improvement in glucose tolerance with a 29.1% reduction of glucose AUC0–2?h in type 2 diabetic mice. All of these results indicated that compound 17 was considered to be a promising lead structure suitable for further optimization.

Discovery of phenylsulfonyl acetic acid derivatives with improved efficacy and safety as potent free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1) has emerged as an attractive anti-diabetic target that mediates glucose-stimulated insulin secretion. Several FFA1 agonists have been reported, but many of them possessed somewhat high lipophilicity and/or molecular weight. Herein, we describe the identification of sulfone-carboxylic acid moiety with the multiple advantages of reducing lipophilicity, cytotoxicity and β-oxidation associated with compound 2. Further structure-activity relationship study based on the previleged scaffolds led to the discovery of 2-{(4-[(2’-chloro-[1,1’-biphenyl]-3-yl)methoxy]phenyl)sulfonyl}acetic acid (compound 20), which showed a better balance than compound 2 in terms of physicochemical properties, cytotoxicity profiles and pharmacokinetic properties. Subsequent in vivo studies demonstrated that compound 20 robustly improves the glucose tolerance both in normal and type 2 diabetic models without the risk of hypoglycemia. Compared to the high risk of TAK-875 induced liver toxicity, there was no significant adverse effects such as hepatic and renal toxicity were observed in the chronic toxicity studies of compound 20 even at the higher dose.

LYSOPHOSPHATIDYLSERINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a lysophosphatidylserine derivative or salt thereof. SOLUTION: The present invention provides a lysophosphatidylserine derivative or salt thereof, or a pharmaceutical composition or lysophosphatidylserine receptor function modulator including the compound or salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

LYSOPHOSPHATIDYLSERINE DERIVATIVE COMPRISING FATTY ACID SURROGATE

PROBLEM TO BE SOLVED: To provide a lysophosphatidylserine derivative to serve as a lysophosphatidylserine receptor function modulator or salt thereof, and a fatty acid surrogate which can be used as a synthetic intermediate of these compounds. SOLUTION: The present invention relates to, for example, a lysophosphatidylserine derivative of the following formula that is obtained by the condensation of the synthetic intermediate 3-(2-((3-(o-tolyloxy)benzil)oxy)phenyl)propanoic acid induced from o-cresol with a corresponding serine phosphoester compound having a hydroxy group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

[7,6]-FUSED BICYCLIC ANTIDIABETIC COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Metal-templated enantioselective enamine/H-bonding dual activation catalysis

An octahedral bis-cyclometalated iridium(III) complex catalyzes the enantioselective α-amination of aldehydes with catalyst loadings down to 0.1 mol%. In this metal-templated design, the metal serves as a structural center and provides the exclusive source of chirality, whereas the catalysis is mediated through the organic ligand sphere. This journal is the Partner Organisations 2014.

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.

Design, synthesis, and biological activity of potent and orally available g protein-coupled receptor 40 agonists

G protein-coupled receptor 40 (GPR40) is being recently considered to be a new potential drug target for the treatment of type 2 diabetes because of its role in the enhancement of free fatty acid-regulated glucose-stimulated insulin secretion in pancreatic β-cells. We initially identified benzyloxyphenylpropanoic acid (1b) (EC50 = 510 nM), which was designed based on the structure of free fatty acids, as a promising lead compound with GPR40 agonist activity. Chemical modification of compound 1b led to the discovery of 3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2- fluorophenyl}propanoic acid (4p) as a potent GPR40 agonist (EC50 = 5.7 nM). Compound 4p exhibited acceptable pharmacokinetic profiles and significant glucose-lowering effects during an oral glucose tolerance test in diabetic rats. Moreover, no hypoglycemic event was observed even after administration of a high dose of compound 4p to normal fasted rats. These pharmacological results suggest that GPR40 agonists might be novel glucose-dependent insulin secretagogues with little or no risk of hypoglycemia.

Discovery of biaryl inhibitors of H+/K+ ATPase

We report the identification of a novel biaryl template for H+/K+ ATPase inhibition. Evaluation of critical SAR features within the biaryl imidazole framework and the use of pharmacophore modelling against known imidazopyridine and azaindole templates suggested that the geometry of the molecule is key to achieving activity. Herein we present our work optimising the potency of the molecule through modifications and substitutions to each of the ring systems. In particular sub-micromolar potency is achieved with (4b) presumably through a proposed intramolecular hydrogen bond that ensures the required imidazole basic centre is appropriately located.