Journal
TETRAHEDRON LETTERS
Volume 58, Issue 38, Pages 3734-3738Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.08.030
Keywords
Dipyridyl diselenide; Selenazolo[5,4-b]pyridine; Diorganyl selenide; Acetylcholinesterase; Antioxidant
Categories
Funding
- CNPq
- CAPES
- FAPERGS [ARD 16/2551-0000358-0, PRONEM 16/2551-0000240-1]
- FINEP
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We describe here an alternative method to prepare bis(2-pyridyl) diselenide derivatives using reduced selenium species, generated in situ, and different 2-chloropyridines promoted by p-TSOH in PEG-400 as solvent. This is a straightforward protocol to prepare bis(3-amino-2-pyridyl) diselenides unprecedented to date. Still, this article describe the employment of synthesized bis(3-amino-2-pyridyl) diselenide and a diverse array of aryl aldehydes to afford the corresponding 2-aryl-selenazolo[5,4-b] pyridines in satisfactory yields and, in a short reaction time under basic condition. Furthermore, when the bis(3-amino-2-pyridyl) diselenide reacted with aliphatic halides, in the presence of NaBH4, a wide range of unsymmetrical diorganyl selenides was obtained. To complete this investigation the bis(3amino-2-pyridyl) diselenide was evaluated for its inhibitory effect on the acetylcholinesterase (AChE) activity and free radical-scavenging capacity. Results demonstrated that this compound was antioxidant and inhibitor of the AChE activity, being a promising therapeutic agent for the treatment of Alzheimer's disease and other neurodegenerative disorders. (C) 2017 Elsevier Ltd. All rights reserved.
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