Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3-triazolyl-thiazolidines Hybrids

An organocatalytic [3+2] cycloaddition reaction between thiazolidine-containing beta-ketoester 1 and aryl azides 2 was employed to synthesize new 1,2,3-triazolyl-thiazolidine hybrids 3. In this metal-free approach, twelve compounds were isolated in yields ranging from 23 % to 96 % by using diethylamine (10 mol%) and DMSO at 75 degrees C for 24 hours. DNA-binding assays were conducted through absorption, emission spectroscopy and viscosimetry analysis, to evaluate the interaction capacity of the studied derivatives with nucleic acids. All the synthesized compounds were evaluated for their interactions with a specific group of compounds containing the pharmacophoric groups triazole and thiazolidine through a molecular docking speculative study, aimed at identifying the interaction profile of these compounds with DNA. The obtained results suggest that 1,2,3-triazolyl-thiazolidine hybrids could be a promising approach in the development of novel therapeutic agents targeting DNA-related processes. The organocatalyzed reaction between thiazolidine-3-carboxylates and aryl azides resulted in the metal-free synthesis of novel 1,2,3-triazolyl-thiazolidine hybrids in good yields. Spectroscopic methods (absorption and emission), viscosimetry, and molecular docking were employed to assess the interactions between the synthesized compounds and DNA, revealing promising results for the development of novel therapeutic agents targeting DNA-related processes. image