The design and synthesis of several new bis-thiazoles 4a-h serving as bis-drugs in comparison with mono-heterocyclic analogs are described. These bis-drugs present superior medicinal and pharmacological activities against both gram-negative (Pseudomonas aeruginosa and Escherichia coli) and gram-positive (Micrococcus luteus and Bacillus subtilis) bacteria, which are in general more sensitive to compounds with higher hydrophobicity. Compounds with higher hydrophobicity (4d and 4h) exhibited some activity against the gram-negative bacteria.
A series of novel bis-thiazoles were synthesized through a one-pot semi-fivecomponent reaction of the prepared α-bisbromo ketones, aldehydes, and thiosemicarbazide in the presence of p-TsOH under reflux condition. Products were obtained in reasonable yields via an efficient, convenient, and simple setup. The inhibitory activity on bacterial growth of the products was studied against Gramnegative (Escherichia coli and Pseudomonas aeruginosa) and Gram-positive bacterial strains (Micrococcus luteus, Staphylococcus aureus) at different concentrations (25, 50, 100, and 200 μg/mL at 600 nm). Most of the products showed inhibitory activity at the concentration of 200 μg/mL. In addition, bis-thiazoles showeed high to moderate antioxidant activity using the diphenylpicrylhydrazyl (DPPH) method. Bis-thiazoles 6i and 6j showed higher antioxidant activity than vitamin C and vitamin E.
A new series of bis‐triazoles has been synthesized through cycloaddition of prepared bis‐azides and diethyl acetylenedicarboxylate in the presence of CuCl2 under solvent‐free condition. Antioxidant activity of products at the concentration of 2000‐62.5 μg/mL using ABTS method was studied and products showed good antioxidant activity. Moreover, IC50 values of products were ranged from 2.00 to 0.06 mM and products 5f‐g and 5i possessed high antioxidant activity and lower IC50 values than ascorbic acid (vitamin C). Also, products 5g and 5e showed the lowest and highest antioxidant activities, respectively. Moreover, in vitro minimum inhibition concentration (MIC) and minimum bactericidal concentration (MBC) of bis‐triazoles were screened against Gram‐positive bacteria strains including Micrococcus luteus and Staphylococcus Gram‐negative bacteria strains including Escherichia coli and Pseudomonas aeruginosa. Most of the products showed a lower MIC than penicillin against tested bacterial strains and also most of the products were active against negative bacterial strains.
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