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

✍ Scribed by Eva Petrlíková; Karel Waisser; Karel Palát; Jiří Kuneš; Jarmila Kaustová

• Book ID: 111491420
• Publisher: Versita
• Year: 2011
• Tongue: English
• Weight: 261 KB
• Volume: 65
• Category: Article
• ISSN: 0366-6352
• DOI: 10.2478/s11696-010-0084-9

✦ Synopsis

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.