Abstract
The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpensive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested compounds, and the cytometry assay indicated low increase in cell numbers in the sub- G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1- phase and the induction of apoptosis was observed.
Highlights
Continuing this study, we present the synthesis and biological activity of conjugates possessing different 2-deoxy-2-iodomonosaccharide scaffolds joined with thiadiazole derivatives
The targeted conjugates were obtained by the addition of the 2-amino-1,3,4-thiadiazole derivative (2) to an unsaturated sugar (1) in the presence of iodine (Scheme 1)
The glycosylation of the glycal derivatives was performed in the dark at room temperature
Summary
1,3,4-Thiadiazole represents an important heterocyclic scaffold due to its pharmacological activity Their derivatives exhibit various and significant activities such as antibacterial [1], antifungal, anti-inflammatory [2], anti-tuberculosis [3], antidepressant [4], and anticancer [5,6,7] activities, etc. The amino derivatives of 1,3,4-thiadiazole, which have different biocidal effects, are investigated, probably due to the toxophore group N=C-S- [8,9,10]. As ligands, they provide many potential binding sites for complexation and have diverse biological activity [11]. Continuing this study, we present the synthesis and biological activity of conjugates possessing different 2-deoxy-2-iodomonosaccharide scaffolds joined with thiadiazole derivatives
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