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Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors
A series of nineteen benzothiazin-4-ones from N-(3-aminopropyl) piperidine, 4-(2-aminoethyl)morpholine or 1-(2-aminoethyl)piperidine, aliphatic or aromatic aldehyde and thiosalicylic acid, were synthesized in good yields by multicomponent one-pot reactions. The solvent was toluene and this efficient...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Taylor & Francis
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263113/ https://www.ncbi.nlm.nih.gov/pubmed/30482059 http://dx.doi.org/10.1080/14756366.2018.1543286 |
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author | Berwaldt, Gabriele A. Gouvêa, Daniela P. da Silva, Daniel S. das Neves, Adriana M. Soares, Mayara S. P. Azambuja, Juliana H. Siqueira, Geonir M. Spanevello, Roselia M. Cunico, Wilson |
author_facet | Berwaldt, Gabriele A. Gouvêa, Daniela P. da Silva, Daniel S. das Neves, Adriana M. Soares, Mayara S. P. Azambuja, Juliana H. Siqueira, Geonir M. Spanevello, Roselia M. Cunico, Wilson |
author_sort | Berwaldt, Gabriele A. |
collection | PubMed |
description | A series of nineteen benzothiazin-4-ones from N-(3-aminopropyl) piperidine, 4-(2-aminoethyl)morpholine or 1-(2-aminoethyl)piperidine, aliphatic or aromatic aldehyde and thiosalicylic acid, were synthesized in good yields by multicomponent one-pot reactions. The solvent was toluene and this efficient procedure afforded the desired heterocycles in 5 h. Identification and characterization were achieved by NMR and GC–MS techniques. In vitro AChE activities of all compounds were evaluated in cerebral cortex and hippocampus of rats and in general, the results in cortex were more promising than hippocampus. The benzothiazinone 5Bd showed the best AChE inhibition activity IC(50) 8.48 μM (cortex) and IC(50) 39.80 μM (hippocampus). The cytotoxicity of seven compounds in MCR-5 human fibroblast cell by SRB test in 24 h were evaluated and 5Bd suggest preliminary safety, showing no cytotoxicity at 100 µM. Finally, these important findings could be a starting point for the development of new AChE inhibitors agents and will provide the basis for new studies. |
format | Online Article Text |
id | pubmed-6263113 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Taylor & Francis |
record_format | MEDLINE/PubMed |
spelling | pubmed-62631132018-12-06 Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors Berwaldt, Gabriele A. Gouvêa, Daniela P. da Silva, Daniel S. das Neves, Adriana M. Soares, Mayara S. P. Azambuja, Juliana H. Siqueira, Geonir M. Spanevello, Roselia M. Cunico, Wilson J Enzyme Inhib Med Chem Short Communication A series of nineteen benzothiazin-4-ones from N-(3-aminopropyl) piperidine, 4-(2-aminoethyl)morpholine or 1-(2-aminoethyl)piperidine, aliphatic or aromatic aldehyde and thiosalicylic acid, were synthesized in good yields by multicomponent one-pot reactions. The solvent was toluene and this efficient procedure afforded the desired heterocycles in 5 h. Identification and characterization were achieved by NMR and GC–MS techniques. In vitro AChE activities of all compounds were evaluated in cerebral cortex and hippocampus of rats and in general, the results in cortex were more promising than hippocampus. The benzothiazinone 5Bd showed the best AChE inhibition activity IC(50) 8.48 μM (cortex) and IC(50) 39.80 μM (hippocampus). The cytotoxicity of seven compounds in MCR-5 human fibroblast cell by SRB test in 24 h were evaluated and 5Bd suggest preliminary safety, showing no cytotoxicity at 100 µM. Finally, these important findings could be a starting point for the development of new AChE inhibitors agents and will provide the basis for new studies. Taylor & Francis 2018-11-27 /pmc/articles/PMC6263113/ /pubmed/30482059 http://dx.doi.org/10.1080/14756366.2018.1543286 Text en © 2018 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group http://creativecommons.org/licenses/by-nc/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial License (http://creativecommons.org/licenses/by-nc/4.0/), which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Short Communication Berwaldt, Gabriele A. Gouvêa, Daniela P. da Silva, Daniel S. das Neves, Adriana M. Soares, Mayara S. P. Azambuja, Juliana H. Siqueira, Geonir M. Spanevello, Roselia M. Cunico, Wilson Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title | Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title_full | Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title_fullStr | Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title_full_unstemmed | Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title_short | Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
title_sort | synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors |
topic | Short Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263113/ https://www.ncbi.nlm.nih.gov/pubmed/30482059 http://dx.doi.org/10.1080/14756366.2018.1543286 |
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