RESUMO
Some thiazolyl hydrazones were synthesized by one pot reaction of thiophene-2-carbaldehyde or 2, 4-dichlorobenzaldehyde, thiosemicarbazide and various phenacyl bromides which were preliminarily screened for in vitro antioxidant and antifungal activities. Excellent DPPH and H2O2 radical scavenged antioxidant activities were observed with almost all the tested compounds. Compounds 4a, 4b, 4c, 4e, 4f and 4i showed comparable DPPH scavenged antioxidant potential (90.26-96.56%) whereas H2O2 scavenged antioxidant activity (90.98-92.08%) was noticeable in case of 4a and 4f; showing significant antioxidant potential comparable with the standard ascorbic acid (95.3%). In vitro antifungal activity of synthesized compounds against fungal species Candida albicance, Aspergillus niger and Aspergillus flavus was found to be moderate to good as compared with the standard fluconazole and MIC values were found in the range of 3.12-25µg/mL. Molecular docking studies revealed that the compounds 4a, 4b and 4c have a potential to become lead molecules in drug discovery process. In silico ADMET study was also performed for predicting pharmacokinetic and toxicity profile of the synthesized antioxidants which expressed good oral drug like behaviour and non-toxic nature.
Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Simulação por Computador , Hidrazonas/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Antioxidantes/síntese química , Antioxidantes/química , Aspergillus flavus/efeitos dos fármacos , Aspergillus niger/efeitos dos fármacos , Candida/efeitos dos fármacos , Relação Dose-Resposta a Droga , Hidrazonas/síntese química , Hidrazonas/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
An ethylene glycol promoted catalyst-free practically efficient and sustainable approach has been developed for the synthesis of several benzylidene-bis-(4-hydroxycoumarin)s and 4,[Formula: see text]-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s by the pseudo three-component reaction of an aldehyde with 4-hydroxycoumarin and 3-methyl-1-phenylpyrazol-5-one, respectively. Inexpensive, non-toxic, and easily available ethylene glycol used as the reaction solvent and promoter renders an efficient protocol in terms of catalyst-free reaction conditions, short reaction time, high yield, practical utility, and green approach.
