RESUMO
New 3-(4-alkylphenyl)-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-(4-alkylphenyl)-2H-1,3-benzoxazine-2,4(3H)-dithiones were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium avium and two strains of Mycobacterium kansasii. The antimycobacterial activity increased with the replacement of the carbonyl group by the thiocarbonyl group in the starting 3-(4-alkylphenyl)-2H-1,3-benzoxazine-2,4(3H)-diones. The most active derivatives were more active than isonicotinhydrazide (INH). Free-Wilson analysis was also carried out and the activity contribution was examined.
Assuntos
Antituberculosos/química , Benzoxazinas/química , Mycobacterium avium/efeitos dos fármacos , Mycobacterium kansasii/efeitos dos fármacos , Mycobacterium tuberculosis/efeitos dos fármacos , Antituberculosos/síntese química , Antituberculosos/farmacologia , Benzoxazinas/síntese química , Benzoxazinas/farmacologia , Isoniazida/farmacologia , Testes de Sensibilidade Microbiana , Relação Estrutura-AtividadeRESUMO
The in vitro biological activity of N-benzylsalicylthioamides was evaluated against eight fungal strains by the broth microdilution method and the results were compared with those obtained with fluconazole. The compounds exhibited an in vitro antifungal activity against the fluconazole-susceptible as well as the fluconazole-resistant fungal strains. The biological activity was analyzed by quantitative structure-activity relationship (QSAR).
Assuntos
Antifúngicos/química , Tioamidas/química , Antifúngicos/farmacologia , Fluconazol/farmacologia , Testes de Sensibilidade Microbiana , Relação Quantitativa Estrutura-Atividade , Tioamidas/farmacologiaRESUMO
New 3-benzyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-benzyl-2H-1,3-benzoxazine-2,4(3H)-dithiones were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. The replacement of the carbonyl group by the thiocarbonyl group increased the antimycobacterial activity. The most active derivatives were more active than isonicotinhydrazide (INH). The cytotoxicity and the antiproliferative activity were studied as well.
Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Benzoxazinas/química , Benzoxazinas/farmacologia , Proliferação de Células/efeitos dos fármacos , Células HeLa , Humanos , Testes de Sensibilidade Microbiana , Mycobacterium/efeitos dos fármacosRESUMO
A gseries of 29 new derivatives of N-benzylsalicylthioamides was synthesized and the compounds were tested for in-vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii, and Mycobacterium avium. The activity was analyzed by quantitative structure-activity relationship (QSAR). Activity increased with increasing lipophilicity and electron donating effect of the substituents in the acyl moiety and decreased with the electrophilic superdelocalizability of the molecules. The most active compounds are more active than isoniazid (INH) and are active against INH-resistant potential pathogenic strains of mycobacterium.
