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N,N-Dimethylthiosemicarbazones of Acetylpyrazines: Preparation and Their Hydrophobic Properties
* 1 , 2 , 1
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: Some substituted acetylpyrazine derivatives were prepared as the starting materials for the subsequent synthesis of N,N-dimethylthiosemicarbazones. General synthetic approach of all newly synthesized compounds is presented. All the N,N-dimethylthiosemicarbazone derivatives of acetylpyrazines 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 values calculated in various ways is discussed as well as the relationships between the lipophilicity and the chemical structure of the studied compounds.
Keywords: <i>N,N</i>-dimethylthiosemicarbazones, Lipophilicity measurement, Structure-lipophilicity relationships