1518-83-8Relevant articles and documents
Dependence of estrogenic activity on the shape of the 4-alkyl substituent in simple phenols
Yamakoshi, Yuko,Otani, Yuko,Fujii, Shinya,Endo, Yasuyuki
, p. 259 - 261 (2000)
The ability of certain chemicals to mimic the effects of natural steroid hormones and their potential to disrupt the delicate balance of the endocrine system in animals has attracted much interest in recent years. Alkylphenolic chemicals have been reported to be weakly estrogenic. Estrogen receptor (ER) binding is primarily the result of interaction of the receptor with both a phenolic residue, and a hydrophobic pharmacophore. We have prepared and screened various phenols having a bulky 4-alkyl group, which may interact hydrophobically with the receptor, for estrogenic activity by using a previously described reporter gene assay employing COS-1 cells transfected with rat ERα-expression plasmid and an appropriate reporter plasmid. Some of the tested compounds, such as 4-(1-adamantyl)phenol and 4-cycloalkylphenols, exhibited much more potent activity than the typical estrogenic alkylphenol, 4-tert-octylphenol.
(2R)-2-Methylchromane-2-carboxylic acids: Discovery of selective PPARα agonists as hypolipidemic agents
Koyama, Hiroo,Boueres, Julia K.,Miller, Daniel J.,Berger, Joel P.,MacNaul, Karen L.,Wang, Pei-Ran,Ippolito, Marc C.,Wright, Samuel D.,Agrawal, Arun K.,Moller, David E.,Sahoo, Soumya P.
, p. 3347 - 3351 (2007/10/03)
A SAR study was conducted on chromane-2-carboxylic acid toward selective PPARα agonisim. As a result, highly potent, and selective PPARα agonists were discovered. The optimized compound 43 exhibited robust lowering of total cholesterol levels in hamster and dog animal models.
Acid-Catalyzed Hydrolysis of Some Secondary Alkyl Phenyl Ethers in Perchloric Acid: Kinetics and Mechanism
Lajunen, Martti,Kaehkoenen, Mika
, p. 726 - 731 (2007/10/02)
Hydrolysis rates and products of isopropyl, cyclopentyl and cyclohexyl phenyl ethers were studied in concentrated aqueous perchloric acid solutions.The activation parameters, solvent deuterium isotope effects, dependences of the reaction rates on acid concentration, substituent effects and products were in agreement with the A-1 mechanism.The pKSH+ values (-6.13 to -5.76) and the slope parameters m* (av. 0.98 +/- 0.03) were measured spectrophotometrically by the excess acidity method.They were used to calculate the m++-parameters (1.46-2.01).Comparisons weremade with the hydrolyses of exo- ad endo-2-norbornyl phenyl ethers and secondary alyl methanesulfonates.
