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Relationship between the Structure and Antimycobacterial Activity of Substituted Salicylanilides
Author(s) -
Waisser Karel,
Bureš Otakar,
Holý Pavel,
Kuneš Jiří,
Oswald Radek,
Jirásková Lucie,
Pour Milan,
Klimešová Věra,
Kubicová Lenka,
Kaustová Jarmila
Publication year - 2003
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200390004
Subject(s) - antimycobacterial , lipophilicity , chemistry , substituent , moiety , stereochemistry , quantitative structure–activity relationship , structure–activity relationship , mycobacterium tuberculosis , mycobacterium kansasii , isoniazid , in vitro , tuberculosis , biochemistry , medicine , pathology
A series of 143 salicylanilides substituted in positions 4 and 5 and in positions 3′ and 4′ was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis , Mycobacterium kansasii , and Mycobacterium avium . To describe the structure‐antimycobacterial activity relationships (QSARs), an approach based on the combination of the Free‐Wilson and Hansch methods was employed (the substituent constants were used in the case of the substituents on the phenyl ring; indicator parameters were used for the substituents on the acyl moiety). The relationships between the antimycobacterial activity and physico‐chemical parameters of all substituents were also explored. The quadratic representation of lipophilicity parameters did not lead to significant correlations.