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Substituted pyrazine-2,5-dicarboxamides: Synthesis, Hydrophobicity Parameters, and Antimycobacterial Evaluation
Published: 30 November 2007 by MDPI in The 11th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products
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