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Substituted pyrazine-2,5-dicarboxamides: Synthesis, Hydrophobicity Parameters, and Antimycobacterial Evaluation
1 , 2 , 3 , * 3
1  Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, 500 05 Hradec Králové, Czech Republic
2  Zentiva a. s., U kabelovny 130, 102 37 Prague 10, Czech Republic
3  Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, 500 05 Hradec Králové, Czech Republic

Abstract: Substituted pyrazine derivatives were synthesized and tested against Mycobacterium tuberculosis strain H37Rv. The hydrophobicity of all the pyrazines was determined using the reversed phase high performance liquid chromatography (RP-HPLC) method (isocratic elution with methanol as an organic modifier in the mobile phase, end-capped non-polar C18 stationary RP column). Experimentally derived Log K values (the logarithm of capacity factor K) were that compared with Log P values calculated by commercially available programmes. The synthetic approach, analytical, spectroscopic, lipophilicity and biological data of ten newly synthesized compounds are presented. Structure—activity relationships among the chemical structure, the anti-mycobacterial activity of the evaluated compounds are discussed. 3-(3-Methylphenyl)-aminopyrazine-2,5-dicarboxamide (7) has shown the highest activity against M. tuberculosis H37Rv (63% inhibition).
Keywords: Pyrazinecarboxamides; In vitro antimycobacterial activity; Lipophilicity determination