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Abstract
In a one pot procedure, a series of novel hybrid heterocycles 6a-g and 7a-g were prepared by condensation of (3aS,4S,6S,6aS)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde 5 with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Compound 5 was prepared from di-acetone D-mannose via a click reaction, primary acetonide deprotection and oxidative cleavage. Characterization of new compounds has been done by IR, NMR, MS and elemental analysis. Anticancer activity of the compounds has also been evaluated.
Highlights
In a one pot procedure, a series of novel hybrid heterocycles 6a–g and 7a–g were prepared by condensation of (3aS,4S,6S,6aS)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde 5 with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions
The synthesis and investigation of biological activity of 1,2,3-triazole glycosides is an important objective, which received a considerable attention by the medicinal chemists
Following the successful introduction of triazoles and thiazolidinones, microwave-assisted multi component reactions (MCRs) reactions, inspired by the biological profile of triazoles, thiazolidinones, and in the continuation of our work on biologically active heterocycles18–29 we have developed a series of novel triazole-linked thiazolidenone derivatives, we have investigated the application of microwave irradiation for the synthesis of our hybrid molecules and evaluated their anticancer activity
Summary
1,2,3-Triazoles are one of the most important classes of heterocyclic organic compounds, which are reported to be present in a plethora of biologically active compounds, useful for diverse therapeutic areas. The 1,2,3-triazole motif is associated with diverse pharmacological activities, such as antibacterial, antifungal, hypoglycemic, antihypertensive and analgesic properties. Polysubstituted five-membered aza heterocycles rank as the most potent glycosidase inhibitors.2 This nucleus in combination with or in linking with various other classes of compounds such as amino acids, steroids, aromatic compounds, carbohydrates etc., became prominent in having various pharmacological properties.3 1,2,3-Triazole modified carbohydrates have became available after the discovery of the Cu(I)-catalyzed azide-alkynes 1,3-dipolar cycloaddition reaction and quickly became a prominent class of non-natural sugar derivatives. The synthesis and investigation of biological activity of 1,2,3-triazole glycosides is an important objective, which received a considerable attention by the medicinal chemists. Synergistic effects are obtained via hybridization of two different bioactive moieties with complementary pharmacophoric functions, or with different modes of action.14 The confirmation of this hypothesis has been well established in previous studies of 4-thiazolidinones coupled with other heterocyclic fragments, i.e. resulting in high anti tumor activity. Following the successful introduction of triazoles and thiazolidinones, microwave-assisted MCR reactions, inspired by the biological profile of triazoles, thiazolidinones, and in the continuation of our work on biologically active heterocycles we have developed a series of novel triazole-linked thiazolidenone derivatives, we have investigated the application of microwave irradiation for the synthesis of our hybrid molecules and evaluated their anticancer activity
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