Antimycobacterial salicylanilides and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones
WAISSER K., GREGOR J., HOLÝ P., KUBICOVÁ L., KLIMEŠOVÁ V., KAUSTOVÁ J. 1
Katedra anorganické a organické chemie Farmaceutické fakulty Univerzity Karlovy, Hradec Králové, Krajská hygienická stanice, Ostrava |
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Summary:
Salicylanilides and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones are strong antimycobacterial substances which can be considered to be potential antituberculotics. In order to be able to verify the
prognostics of the relationships between the structure and antimycobacterial activity, the series of
previously evaluated substances was extended to include 4´-ethoxycarbonylsalicylanilide, 4´-tri-
fluoromethylsalicylanilide,
4´-cyanidosalicylanilide,
4´-thiocarbamoylsalicylanilide, 3-(4-ethoxycar-
bonylphenyl)-2H-1,3-benzoxazine-2,4(3H)-dione, 3-(4-trifluoromethylphenyl)-2H-1,3-benzoxazine-
-2,4(3H)-dione, and 3-(4-cyanidophenyl)-2H-1,3-benzoxazine-2,4-(3H)-dione. The substances were
evaluated against Mycobacterium tuberculosis, M. kansasii, and M. avium. In harmony with the
previous study (see ref. 1), antimycobacterial activity increased with increasing lipophilicity and
electron-acceptor properties of substituents. As the values of regression coefficients were not
substantially changed after the complementation of the group, the present authors consider the
problem under study to be solved.
Key words:
salicylanilides - benzoxazine -Œ mycobacterium - tuberculostatic - QSAR
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