A simple method for the synthesis of 4-arylselanyl-7-chloroquinolines used as in vitro acetylcholinesterase inhibitors and in vivo memory improvement

作者：Duarte Luis Fernando B; Barbosa Eduardo S; Oliveira Renata L; Pinz Mikaela P; Godoi Benhur; Schumacher Ricardo F; Luchese Cristiane; Wilhelm Ethel A^*; Alves Diego^*

来源：Tetrahedron Letters, 2017, 58(33): 3319-3322.

DOI：10.1016/j.tetlet.2017.07.039

• Nitrogen heterocycles
• Quinolines
• Selenium
• Acetylcholinesterase
• Memory

We described here an alternative method for the synthesis of 4-arylselanyl-7-chloroquinolines through reactions of 4,7-dichloroquinoline with organylselenols, generated in situ by the reaction of diorganyl diselenides with H3PO2 (50 wt% in H2O). These reactions proceeded efficiently at 60 degrees C under N-2 atmosphere and are suitable to a range of diorganyl diselenides containing electron-donating and electron-withdrawing groups, affording the corresponding 4-aryl-7-chloroquinolines in high yields. The synthesized compounds were screened for their in vitro acetylcholinesterase (AChE) activity and our results demonstrated that the 7-chloro-4-[(4-fluorophenyl)selanyl]quinoline inhibited the AChE activity and improved memory in mice, making this compound is a potential therapeutic agent for the treatment of Alzheimer disease and other neurodegenerative disorders.

• 出版日期2017-8-16