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Synthesis and Hydrophobic Properties of Substituted 2-Aryl-5,7-di-tert-butylbenzoxazoles
* 1 , 2 , 1
1  Zentiva a. s., U kabelovny 130, 102 37 Prague 10, Czech Republic
2  Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Kralove, 500 05 Hradec Kralove, Czech Republic

Abstract: The series of twenty lipophilic 2-aryl-5,7-di-tert-butylbenzoxazoles substituted in the phenyl ring was prepared by the reaction of 2-amino-4,6-di-tert-butylphenol with the appropriated aldehydes. The general synthetic approach of all newly synthesized compounds is presented. All the substituted 5,7-di-tert-butylbenzoxazole derivatives were analyzed using the reversed phase high performance liquid chromatography (RP-HPLC) method for the lipophilicity measurement. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP column. In the present study the correlation between RP-HPLC retention parameter log K (the logarithm of capacity factor K) and log P data calculated in various ways is shown. The relationships between the lipophilicity and the chemical structure of the studied compounds are discussed as well.
Keywords: 2-amino-4,6-di-<i>tert</i>-butylphenol, 2-Aryl-5,7-di-<i>tert</i>-butylbenzoxazoles, Lipophilicity measurement, Structure-lipophilicity relationships