RESUMO
N,N'-Diarylethylene-bis-thiourea derivatives 1 and 8 were synthesized and their reactions with hydrazonoyl chlorides yielded the corresponding bis-(2-(N-arylimino)-1,3-thiazolidine derivatives 5a-d and 11a-c. The reaction of compound 1 with several α-haloketones afforded the bis-(5-methyl-2-(N-phenylimino)-1,3-thiazolidine derivatives 15a-c and 19a, b. The newly synthesized compounds were tested for their antimicrobial activity against four fungi, two Gram-positive and two Gram-negative bacteria and showed high antibacterial and antifungal activities against all the test microorganisms except Pseudomonas aeruginosa and Candida albicans. Compounds 5b, 15b and 19a exhibited the highest activities against the test microorganisms. The MIC evaluation showed that compound 15b has higher activity than Amphotericin B and Ampicillin against all tested fungi and Gram-positive bacteria (Staphylococcus pneumonia) and showed similar activity like Ampicillin against Gram-negative bacteria (Escherichia coli).
Assuntos
Antibacterianos/síntese química , Antibacterianos/farmacologia , Antifúngicos/síntese química , Antifúngicos/farmacologia , Tiazóis/síntese química , Tiazóis/farmacologia , Antibacterianos/química , Antifúngicos/química , Bactérias/efeitos dos fármacos , Relação Dose-Resposta a Droga , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-Atividade , Tiazóis/químicaRESUMO
New 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine and 1,3-thiazole derivatives incorporating indole nucleus were prepared using 3-acetylindole as precursor and evaluated for their antiviral activity against herpes simplex type 1 (HSV-1).
Assuntos
Antivirais/síntese química , Antivirais/farmacologia , Herpes Simples/tratamento farmacológico , Herpesvirus Humano 1/efeitos dos fármacos , Indóis/síntese química , Indóis/farmacologia , Tiazóis/síntese química , Tiazóis/farmacologia , Animais , Antivirais/química , Sobrevivência Celular/efeitos dos fármacos , Chlorocebus aethiops , Compostos Heterocíclicos/síntese química , Compostos Heterocíclicos/química , Compostos Heterocíclicos/farmacologia , Humanos , Indóis/química , Tiazóis/química , Células VeroRESUMO
Benzo[d]imidazole 3 and 1,2,4-triazin-5(2H)-one 6 were prepared by the reaction of starting ethyl (3-hydroxy-1H-inden-2-yl)(oxo)-acetate 2 with o-phenylenediamine and thiosemicarbazide respectively. Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. The reactivity of hydrazide 8 towards fluorinated aldehyde, phthalic anhydride, and hydrazonoyl chlorides 15a, b was studied to give fluorinated hydrazones, imide bis-hydrazones 13-16. The newly synthesized compounds were screened for their cytotoxic activities and compounds 6, 8, 9 and 10 were found the most potentially cytotoxic. The detailed synthesis, spectroscopic and biological data are reported.