RESUMO
3 Starting from 2-methyl-4-nitro-imidazole, new 5-(2-methyl- 4-nitro-1-imidazomethyl)-1,3,4-oxadiazole-2-thione () was synthesized and was subjected to Mannich reaction with appropriate amines to yield a new series of 3-substituted aminomethyl-5-(2-methyl-4-nitro-1-imidazomethyl)- 1,3,4-oxadiazole-2-thiones (4a-j). The structure of the title compounds was elucidated by elemental analysis and spectral data. The newly synthesized Mannich bases were screened for their antibacterial and antifungal activity. Many of these compounds exhibited potent antifungal activity.
Assuntos
Antifúngicos , Imidazóis , Bases de Mannich , Oxidiazóis , Antifúngicos/síntese química , Antifúngicos/química , Antifúngicos/farmacologia , Técnicas de Química Sintética/métodos , Inibidores Enzimáticos/agonistas , Inibidores Enzimáticos/química , Imidazóis/agonistas , Imidazóis/síntese química , Imidazóis/química , Imidazóis/farmacologia , Bases de Mannich/síntese química , Bases de Mannich/química , Bases de Mannich/farmacologia , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Fungos Mitospóricos/efeitos dos fármacos , Oxidiazóis/síntese química , Oxidiazóis/química , Oxidiazóis/farmacologia , Staphylococcus/efeitos dos fármacos , Relação Estrutura-AtividadeRESUMO
On account of the reported anticancer activity of triazolothiadiazines, we have synthesized a novel series of 6-arylsubstituted-3-[2-(4-substitutedphenyl)propan-2-yl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and tested for in-vitro cytotoxicity by trypan blue exclusion and MTT assay. These compounds were also evaluated for their in-vivo anthelmintic activity, as well as in-vitro antimicrobial studies. Amongst the tested compounds, the compound 7j was the most promising cytotoxic agent with IC(50) value of 10.54µM in MCF-7 cells. The compounds 7l and 7q exhibited excellent anthelmintic activity. The compounds 7d, 7f, 7j, 7l, 7o, 7p and 7r showed good antibacterial activity, whereas compounds 7e and 7k exhibited excellent antifungal activity. The structures of newly synthesized compounds were characterized by IR, (1)H NMR, (13)C NMR and LCMS analysis.
Assuntos
Anti-Helmínticos/síntese química , Anti-Infecciosos/síntese química , Antineoplásicos/síntese química , Citotoxinas/síntese química , Tiadiazinas/síntese química , Triazóis/síntese química , Animais , Anti-Helmínticos/farmacologia , Anti-Infecciosos/farmacologia , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Citotoxinas/farmacologia , Fungos/efeitos dos fármacos , Fungos/crescimento & desenvolvimento , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Humanos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Oligoquetos/efeitos dos fármacos , Oligoquetos/crescimento & desenvolvimento , Espectrofotometria Infravermelho , Tiadiazinas/farmacologia , Triazóis/farmacologia , Azul TripanoRESUMO
On account of the reported anticancer activity of pyrazoles and oxadiazoles, we have designed and synthesized a novel combinatorial library of S-substituted-1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety and tested for in-vitro cytotoxic activity by MTT assay. Amongst the tested compounds, the compound 5e was the most promising anticancer agent with IC(50) value of 15.54 µM in MCF-7 cells, compared to Doxorubicin as standard drug. The newly synthesized compounds were characterized by NOE, IR, (1)H NMR, (13)C NMR and LC-MS analysis.