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Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation
; Department of Chemistry, Faculty of Sciences, Taibah University, PO Box 344, Al-Madinah Al-Munawarah, Saudi Arabia
MOHAMED REDA AOUAD
; Laboratoire de Chimie and Electrochimie des Complexes Métalliques (LCECM), Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, USTO-MB, PO Box 1505, Oran, El M’nouar, Algeria
Puni tekst: engleski, pdf (380 KB)
REZKI, Z., AOUAD, M.R. (2017). Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation. Acta Pharmaceutica, 67(3). doi:10.1515/acph-2017-0024
The present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles 4a-e through a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involves in situ generation of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates 6a-o were recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.
benzothiazoles; 1,2,3-triazoles; 1,2,4-triazoles; click synthesis; antimicrobial
Hrčak ID: 181145
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