Efficient palladium-catalyzed C-S cross-coupling reaction of benzo-2,1,3-thiadiazole at C-5-position: A potential class of AChE inhibitors |
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Authors: | Beatriz F. dos Santos Caroline F. Pereira Mikaela P. Pinz Aline R. de Oliveira George Brand Ramesh Katla Ethel A. Wilhelm Cristiane Luchese Nelson L.C. Domingues |
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Affiliation: | 1. Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil;2. Programa de Pós-Graduação em Bioquímica e Bioprospecção, Laboratório de Pesquisa em Farmacologia Bioquímica (LaFarBio), Grupo de pesquisa em Neurobiotecnologia – GPN, CCQFA, Universidade Federal de Pelotas, Pelotas/RS, Brazil |
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Abstract: | Functionalization of 2,1,3-benzothiadiazole (BTD) with thiols at C-5 position remains low explored. Moreover, the arylthiol-substitutions at this position are also unexplored and can not be found by a SN2 or SN1 reaction. In this sense, herein we present a new palladium-catalyzed methodology for a wide variety of unpublished 5-arylsulfanyl-benzo-2,1,3-thiadiazole derivatives synthesis with moderate to high yields using a low catalytic loading of Pd(L-Pro)2 as low-coast, and efficient catalyst in low reaction time. Besides, we concluded that the pKa of thiol species has an important role in this catalysis, mainly in the CMD like catalytic cyclo process, which strongly interferes in the reaction yields. Furthermore, arylsulfanyl-benzo-2,1,3-thiadiazoles derivatives have been assessed (in vitro) as potential acetylcholinesterase inhibitors. |
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Keywords: | acetylcholinesterase inhibitors Arylsulfanyl-benzo-2,1,3-thiadiazole cross-coupling C-S bond |
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