Organoselenium compounds from purines: Synthesis of 6-arylselanylpurines with antioxidant and anticholinesterase activities and memory improvement effect

Abstract

We describe here a simple method for the synthesis of 6-arylselanylpurines with antioxidant and anticholinesterase activities, and memory improvement effect. This class of compounds was synthesized in good yields by a reaction of 6-chloropurine with diaryl diselenides using NaBH as reducing agent and PEG-400 as solvent. Furthermore, the synthesized compounds were evaluated for their in vitro antioxidant and acetylcholinesterase (AChE) inhibitor activities. The best AChE inhibitor was assessed on the in vivo memory improvement. Our results demonstrated that the 6-((4-chlorophenyl)selanyl)-9H-purine and 6-(p-tolylselanyl)-9H-purine presented in vitro antioxidant effect. In addition, 6-((4-fluorophenyl)selanyl)-9H-purine inhibited the AChE activity and improved memory, being a promising therapeutic agent for the treatment of Alzheimer's disease.

System-oriented optimization of multi-target 2,6-diaminopurine derivatives: Easily accessible broad-spectrum antivirals active against flaviviruses, influenza virus and SARS-CoV-2

“…The induction of oxidative stress is in fact recognized as a common trigger of exacerbation in diseases caused by different viruses, including flavivirus, coronavirus and, particularly, Influenza virus [ 27 ]. A few literature reports show that opportune functionalization of the purine scaffold can lead to derivatives also endowed with antioxidant properties by scavenging reactive oxygen species (ROS) [ [28] , [29] , [30] ]. Among the many possible functionalization options, we were intrigued by a recent work from the Feringa group, describing the development of photoswitchable purine derivatives bearing an azobenzene moiety in C6 [ 31 ].…”

Selenides and Diselenides: A Review of Their Anticancer and Chemopreventive Activity

“…Prevention of oxidative damage and radical scavenging potential were found for the indol-selenide derivative 51 [ 88 ] and the 6-arylselanylpurines 52a and 52b [ 89 ], respectively. Apart from preventing oxidative stress, compound 51 did not show hepatic, renal or cerebral toxicity.…”

A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation

“…It is found in foods (e.g., tuna, sardines beans, spinach, Brazil nuts) as well as in the structure of different proteins, i.e., selenoproteins [ 3 , 4 ]. The latter is crucial for the chemoprotection of cells from infection, inflammation, and oxidative damage [ 5 , 6 , 7 , 8 , 9 , 10 ]. Importantly, the body–Se balance is fundamental for the maintenance of the immune system’s regular function and antimicrobial defense [ 7 , 8 , 10 ].…”