RESUMO
Abstract Dramatically increased occurrence of both superficial and invasive fungal infections has been observed. Candida albicans appear to be the main etiological agent of invasive fungal infections. The anti-C. albicans activity of thiosemicarbazide, 1,3,4-Thiadiazole, and 1,2,4-triazole-3(4H)-thione compounds (compounds 3-23) were investigated. The MIC values of thiadiazole and triazole derivatives 10-23 were in the range of 0.08-0.17 µmol mL-1, while that of fluconazole was 0.052 µmol mL-1. Compound 11 (5-(2-(4-chlorobenzyloxy)phenyl)-N-allyl-1,3,4-thiadiazol-2-amine) and compound 18 (5-(2-(4-chlorobenzyloxy)phenyl)-4-allyl-2H-1,2,4-triazole-3(4H)-thione) were found to be the most active compounds, with MIC values of 0.08 µmol mL-1. The newly synthesized thiadiazole and triazole compounds (compounds 10-23) showed promising anti-Candida activity. The allyl substituent-bearing compounds 11 and 18 exhibited significant anti-Candida albicans activity and showed a binding mode as well as the fluconazole x-ray structure.
Assuntos
Tiadiazóis/síntese química , Triazóis/síntese química , Candida albicans/isolamento & purificação , Salicilatos/farmacologia , Simulação de Acoplamento Molecular , Infecções Fúngicas Invasivas/prevenção & controleRESUMO
Thiadiazoles are their derivatives exhibit a wide variety of pharmacological activities such as Antibacterial and anti-inflammatory. In the present study we have synthesized derivatives some 2,5 substituted 1,3,4-thiadiazoles. The structures of these synthesized compounds were confirmed by IR, NMR, and MASS spectra data. These compounds were evaluated for varies biological activities such as antibacterial and anti-inflammatory activity
Assuntos
Animais de Laboratório , Masculino , Feminino , Tiadiazóis/síntese química , Ratos Endogâmicos , Espectrofotometria Infravermelho , Staphylococcus aureus/efeitos dos fármacos , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Estrutura Molecular , Anti-Inflamatórios não Esteroides/síntese química , Aspergillus niger/efeitos dos fármacos , Benzamidas/síntese química , Espectroscopia de Ressonância MagnéticaRESUMO
This study was designed to synthesize chemically 2-aminothiadiazole derivatives and conversion to Schiffs base. The principle synthesis of these compounds was to involve three steps: First: by thermal cyclization of thiosemicarbazied with carbon disulfide in the presence of potassium hydroxide dissolved in anhydrous ethanol to yield 2-amino-5- mercapto-l,3.4-thiadiazole. Second: by thermal cyclization ofthiosemicarbazied with substituted carboxylic acid and sulphuric acid, to yield 2-amino-5-R-I,3,4-thiadiazole. Third: Schiff 's base formation by reflux of aromatic aldehyde with 2-amino-5-R-l, 3, 4-thiadiazole in the presence of ethanol. The chemical structures of all prepared compounds were confirmed by spectral data [UV-visible and 1 R spectroscopy] tables [1, 2, and 3]
Assuntos
Tiadiazóis/síntese químicaRESUMO
The p-nitrophenylhydrazone of dehydro-L-ascorbic acid [I] reacted with methylhydrazine in MeOH giving the pyrazolinedione [V] and not the expected mixed bishydrazone [III]. The pyrazole derivative gave the tri-O-acetyl and tri-O-benzoyl derivatives [VI] and [VII], respectively. Periodate oxidation of [V] gave the 3-arboxaldehyde derivative [VIII] which was reduced by NaBH4 to the corresponding alcohol [IX] which formed the monoacetyl derivative [X]. The 3-carboxaldehyde condensed with hydroxylamine to give the 3-hydroxyiminomethyl derivative [XI], which upon acetylation gave the 3-acetoxyiminomethyl derivative [XII]. Similarly, benzoylation of [XI] gave the 3-benzoyl derivative [XIII]. The 3-thiosemicarbazone [XIV] of [VIII] gave the bicyclic derivative [XV] upon treatment with benzoyl chloride in pyridine. Treatment of [XV] with hydrazine hydrate gave [XVII]. which upon benzoylation gave [XVIII]