77182-74-2

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 62290-50-0 methyl 4-(4-methoxybenzyloxy)benzoate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 150-76-5 4-methoxy-phenol 
• 77182-73-1 4-[(4-methoxyphenyl)methoxy]benzaldehyde 

Downstream Products

• 343221-64-7 4-Methoxy-1-(4-chloromethyl-phenoxymethyl)-benzene 
• 1619258-71-7 p-methoxybenzyl-4-oxybenzyl phenyl sulfide 
• 613240-53-2 {7-[4-(4-Methoxy-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic Acid Methyl Ester 
• 77182-72-0 4-(4'-methoxybenzyloxy)benzyl methyl ether 

Relevant academic research and scientific papers

Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) δ agonists

A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (α, δ, and γ) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC50 = 10 nM) and selectivity (120-fold) for PPARδ over PPARα. Many of the analogs investigated were found to be highly selective for PPARδ and were dependent on the point of attachment of the substituent. In the 1,4-series, analog 28e was found to be the most potent (IC50 = 1.7 nM) and selective (>1000-fold) compound for PPARδ. None of the compounds tested showed appreciable binding affinity for PPARγ.

Compounds that modulate PPAR activity and methods for their preparation

This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing disipidemia, hypercholesteremia, obesity, eating disorders, hyperglycemia, atherosclerosis, hypertriglyceridemia, hyperinsulinemia and diabetes in a mammal as well as methods of supressing appetite and modulating leptin levels in a mammal. The present invention also discloses methods for making the disclosed compounds.

Methanolysis (Solvolysis) and Synthesis of 4'-Substituted 4-Benzyloxybenzyl Chlorides and Some Related Compounds: Comparisons with the Corresponding Benzoyl Compounds

The kinetics of methanolysis (solvolysis) in 97.4percent MeOH-dioxan of a series of 4'-substituted 4-benzyloxybenzyl chlorides, and of 4-anisyl, 4-phenoxybenzyl, and benzyl chlorides have been studied and discussed, including comparisons with the data for the corresponding series of benzoyl chlorides, previously reported by us.The 4'-substituted precursor alcohols, chlorides, and product methyl ethers are all new compounds. 4-Anisyl chloride and the series of benzyloxybenzyl chlorides react by the SN1 mechanism, whereas benzyl chloride react by the SN2 mechanism. 4-Phenoxybenzyl chloride shows intermediate behaviour.A similar pattern was observed with the corresponding benzoyl compounds.In both series the reactivity order is CH3O > 4'-CH3C6H4CH2O (-0.76) >C6H5CH2O (-0.74) > 4'-ClC6H4CH2O (-0.69) > 4'-NO2C6H4CH2O (-0.60) > C6H5O > H (values in paranthesis are new ?+ values).At 25 deg C the overall range of rates is 4290 in the benzyl series, compared with only 2.42 in the benzyl series.The Arrhenius parameters in the two series demonstrate, however, an underlying similarity with obvious differences superimposed.In both series, the introduction of 4-OR groups leads to a ΔS increase of ca. 40 J mol-1 K-1.In the benzyl series this is accompanied by ΔE decreases of ca. 6-10 kJ mol-1 whereas in the benzoyl series ΔE values increase by ca. 10-15 kJ mol-1.The equation log k = log k0 + n in mixtures with increasing content of dioxan, was used to study the rate dependence on MeOH concentration.Values of n are ca. 5 between 97.4 and 8.3percent MeOH, and ca. 3 between 83.3 and 50.0percent MeOH.