1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation

Herein we report the design, synthesis and characterization of novel 1,2,4-triazole d-ribose derivatives, as well as their synthetic precursors.The antitumoral activity against T cell lymphoma cell line of these products was studied. Structures containing a 1,2,4-triazolic ring linked by sulfur to the carbohydrate moiety showed a moderate antiproliferative activity. The presence of the second heterocyclic ring did not show significant changes in their biological activity. Meanwhile, structures with 3-thiobenzyl-5-substituted-1,2,4-triazole ring linked by nitrogen leads to compounds with a biphasic behavior, stimulating cell proliferation at low concentrations and inhibiting it at higher ones. An increment in the polarity was associated with a decrease in the activity of the evaluated compounds.A preliminary antitumoral screening pointed the 1,2,4-triazolic structures linked to protected sugars as promising leaders for further studies.

Graphical abstractNovel 1,2,4-triazole d-ribose derivatives were synthesized and their antitumoral activity on a T cell lymphoma cell line was evaluated.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of novel 1,2,4-triazole d-ribose derivatives. ► Antitumoral activity on a T cell lymphoma cell line was evaluated. ► Triazole ring linked by sulfur to protected sugar shows antiproliferative activity. ► The antiproliferative activity decreases as polarity increase. ► Isoxazoline ring, as a second heterocycle has no relevance in the activity.