ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides
Eva Petrlíková, Karel Waisser, Karel Palát, Jiří Kuneš, and Jarmila Kaustová
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, CZ-50003 Hradec Králové, Czech Republic
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.
Keywords: salicylamide – picoline – lipophilicity – TLC – QSAR – antimycobacterial activity
Full paper is available at www.springerlink.com.
Chemical Papers 65 (1) 52–59 (2011)
Saturday, September 23, 2023