In the last decades, organoselenium compounds gained interest due to their important biological features. However, the lack of solubility, which characterizes most of them, makes their actual clinical exploitability a hard to reach goal. Selenosugars, with their intrinsic polarity, do not suffer from this issue and as a result, they can be conceived as a useful alternative. The aim of this review is to provide basic knowledge of the synthetic aspects of selenosugars, selenonium salts, selenoglycosides, and selenonucleotides. Their biological properties will be briefly detailed. Of course, it will not be a comprehensive dissertation but an analysis of what the authors think is the cream of the crop of this interesting research topic.
We described here our results on the use of thiourea as a ligand in the copper catalysed azide‐alkyne cycloaddition (CuAAC) of 2‐azidobenzaldehyde with alkynes. Reactions were performed reacting 2‐azidobenzaldehyde with a range of terminal alkynes using 10 mol % of copper iodide as a catalyst, 20 mol % of thiourea as a ligand, triethylamine as base, DMSO as solvent at 100 °C under nitrogen atmosphere. The corresponding 2‐(1H‐1,2,3‐triazoyl)‐benzaldehydes (2‐TBH) were obtained in moderated to excellent yields and according our experiments, the use of thiourea decreases the formation of side products. The obtained compounds were screened for their binding affinity with multiple therapeutic targets of AD by molecular docking: β‐secretase (BACE), glycogen synthase kinase (GSK‐3β) and acetylcholinesterase (AChE). The three compounds with highest affinity, 5 a (2‐(4‐phenyl‐1H‐1,2,3‐triazol‐1‐yl)benzaldehyde), 5 b (2‐(4‐(p‐tolyl)‐1H‐1,2,3‐triazol‐1‐yl)benzaldehyde), and 5 d (2‐(4‐(4‐(tert‐butyl)phenyl)‐1H‐1,2,3‐triazol‐1‐yl)benzaldehyde) were selected and evaluated on its antioxidant effect, in view of select the most promising one to perform the in vivo validation. Due the antioxidant potential ally to the affinity with BACE, GSK‐3β and AChE, compound 5 b was evaluated in a mouse model of AD induced by intracerebroventricular injection of streptozotocin (STZ). Our results indicate that 5 b (1 mg/kg) treatment during 20 days is able to reverse the cognitive and memory impairment induced by STZ trough the modulation of AChE activity, amyloid cascade and GSK‐3β expression.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.