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SYNTHESIS AND STUDY OF α-GLUCOSIDASE INHIBITION, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF SOME BENZIMIDAZOLE DERIVATIVES CONTAINING TRIAZOLE, THIADIAZOLE, OXADIAZOLE, AND MORPHOLINE RINGS

E. Menteşe, S. Ülker, B. Kahveci
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Abstract


A new series of 2-(4-bromobenzyl)- and 2-(4-fluorobenzyl)-1H-benzimidazole derivatives containing 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole, and morpholine rings have been synthesized. The structures of newly synthesized compounds were confirmed by 1H and 13C NMR and mass spectra, and all substances have been screened for their α-glucosidase inhibition, antimicrobial, and antioxidant activities. Hydrazide, oxadizole, thiosemicarbazide, and 1,2,4-triazol-3-thiol derivatives showed very good ABTS scavenging activities (IC50 1.94–4.79 μM). Oxadiazole and thiosemicarbazide derivatives also revealed notable DPPH scavenging activity. 5-[(2-(4-Bromobenzyl)-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol was found to be more potent than acarbose. 2-(4-Fluorobenzyl)-1H-benzimidazole was effective against both Gram-positive and Gram-negative bacteria, and, especially, M. smegmatis.

How to Cite
Menteşe, E.; Ülker, S.; Kahveci, B. Chem. Heterocycl. Compd. 2015, 50, 1671. [Khim. Geterotsikl. Soedin. 2014, 1820.]

For this article in the English edition see DOI 10.1007/s10593-015-1637-1


Keywords


benzimidazole; 1,3,4-oxadiazole; 1,2,4-triazole; 1,3,4-thiadiazole; antimicrobial activity; antioxidant activity; α-glucosidase inhibition

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