Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles

Bioorganic & Medicinal Chemistry
Anelia Ts MavrovaAndrija Smelcerovic

Abstract

Two groups of benzimidazole derivatives were synthesized using as precursors 5(6)-substituted 2-mercapto-benzimidazol-thiols and their antioxidant activity was investigated using TBA-MDA test. In the group of 1,3-disubstituted-benzimidazol-2-imines the highest lipid peroxidation inhibition effect 74.04% (IC₅₀=141.89 μg/mL) revealed ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimdazol-1-yl]acetate 12 while in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC₅₀=53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G(∗∗) level and the respective bond dissociation enthalpies were calculated. The appropriate models for the HAT and SET-mechanism of the antioxidant activity were proposed. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and three Gram-negative bacteria (Escherichia coli ATCC 8739, Pseudomo...Continue Reading

Citations

Mar 28, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hülya Karaca GençerYusuf Öztürk
Apr 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Emanuel Hernández-NúñezGabriel Navarrete Vázquez
Jul 29, 2018·Journal of Cellular Biochemistry·Ana KolarevićAndrija Šmelcerović
Jul 30, 2020·European Journal of Medicinal Chemistry·Kashif HaiderM Shahar Yar

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