A simple method for the synthesis of 4-arylselanyl-7-chloroquinolines used as in vitro acetylcholinesterase inhibitors and in vivo memory improvement |
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| Authors: | Luis Fernando B. Duarte Eduardo S. Barbosa Renata L. Oliveira Mikaela P. Pinz Benhur Godoi Ricardo F. Schumacher Cristiane Luchese Ethel A. Wilhelm Diego Alves |
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| Affiliation: | 1. Laboratório de Síntese Orgânica Limpa, LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil;2. Programa de Pós-Graduação em Bioquímica e Bioprospecção, Laboratório de Pesquisa em Farmacologia Bioquímica, Grupo de Pesquisa em Neurobiotecnologia – GPN, CCQFA Universidade Federal de Pelotas, UFPel, Pelotas, RS, Brazil;3. Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Universidade Federal da Fronteira Sul – UFFS, Cerro Largo, RS, Brazil |
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| Abstract: | 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 °C under N2 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. |
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| Keywords: | Nitrogen heterocycles Quinolines Selenium Acetylcholinesterase Memory |
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