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Synthesis and Hydrophobic Properties of Some Substituted 3-Arylaminopyrazine-2,5-dicarbonitriles
* 1 , 2 , 2
1  Zentiva a. s., U kabelovny 130, 102 37 Prague 10, Czech Republic
2  Department of Pharmaceutical Chemistry and Drug Control, Charles University in Prague, Faculty of Pharmacy in Hradec Kralove, 500 05 Hradec Kralove, Czech Republic

Abstract: The series of thirteen mono-substituted 3-arylaminopyrazine-2,5-dicarbonitriles was prepared by the reaction of 3-chloropyrazine-2,5-dicarbonitrile with the appropriated anilines. The general synthetic approach of all newly synthesized compounds is presented. All the substituted 3-arylaminopyrazine-2,5-dicarbonitriles, which showed significant antifungal and antimycobacterial activity, 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: 3-Arylaminopyrazine-2,5-dicarbonitriles, Lipophilicity measurement, Structure-lipophilicity relationships