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A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides

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Abstract

As a part of our systematic study of antimycobacterially active derivatives of salicylamides, a series of nineteen derivatives of N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides was synthesised. The compounds exhibited in vitro activity against Mycobacterium tuberculosis and M. avium. Their lipophilicity, R M, was measured by thin layer chromatography on silica gel impregnated with trioctadecylsilane and the logarithm of the partition coefficient (octanol-water), logP, was calculated. Both the parameters of lipophilicity correlated. The quantitative relationship between the structure and antimycobacterial activity was calculated. Antimycobacterial activity increased with an increase in lipophilicity. The N-(2-pyridylmethyl)salicylamide derivatives were more active than the derivatives of isomeric N-(3-pyridylmethyl)salicylamides. The geometry of compounds was calculated and the calculation was verified by measuring the length of the hydrogen bond between hydroxyl and carbonyl groups on the salicylic moiety.

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Authors and Affiliations

  1. Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, CZ-50003, Hradec Králové, Czech Republic

    Eva Petrlíková, Karel Waisser, Karel Palát & Jiří Kuneš

  2. Regional Institute of Public Health, Partyzánské náměstí 7, CZ-70200, Ostrava, Czech Republic

    Jarmila Kaustová

Authors
  1. Eva Petrlíková
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  2. Karel Waisser
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  3. Karel Palát
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  4. Jiří Kuneš
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  5. Jarmila Kaustová
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Correspondence to Eva Petrlíková.

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Petrlíková, E., Waisser, K., Palát, K. et al. A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides. Chem. Pap. 65, 52–59 (2011). https://doi.org/10.2478/s11696-010-0084-9

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  • DOI: https://doi.org/10.2478/s11696-010-0084-9

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