Novel Symmetrical 1,4-Disubstituted-bis-1,2,3-Triazoles: Synthesis by Double CuAAC and Cytotoxicity Evaluation

Abstract

Background: A series of symmetrical 1,4-disubstituted bis-1,2,3-triazoles was prepared by double copper catalyzed Azide-alkyne Cycloaddition (CuAAC) from aliphatic bis-azides and a tetraethylene glycol bis-azide derivative. The eighteen novel compounds were evaluated in vitro for their cytotoxic activity against two human tumor cell lines: Human breast adenocarcinoma (MDA-MB 231) and ovarian adenocarcinoma (TOV-21G). Results and Conclusion: The results of colorimetric MTT assays showed that compounds 4j and 4q exhibited a better selectivity index and cell viability comparable with the standard drug doxorubicin. These compounds induced apoptosis in both tested cell lines, as assessed by BrdU assay. The results suggest that these structurally simple compounds may be promising prototypes for antitumoral agents.

Metal-Free Route to Carboxylated 1,4-Disubstituted 1,2,3-Triazoles from Methoxycarbonyl-Modified Vinyl Sulfone

“…1,4-cDT derivative 5 was studied as a new α-glucosidase inhibitor . A limited number of bis- or poly 1,4-cDTs have also been synthesized and studied . A series of geminal carboxylated tristriazole compounds have been prepared, and the six ester groups in the periphery of the nitrogen-rich system 6a provided the starting material for dendritic structures .…”

“…It should be noted that all these carboxylated triazoles barring one set 1b were synthesized using the CuAAC strategy (Figure ). , The requisite metal catalyst has imposed limitation of the CuAAC concept in areas such as chemical biology and photophysical chemistry. As a consequence, metal-free alternative routes to the regioselective formation of 1,4-DTs were looked into, although general methods are limited in the literature .…”