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Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy
Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized imidazo pyranotacrines as non-hepatotoxic, multipotent tacrine analogues. Among these compounds, 1-(5-amino-2-methyl-4-(1-methyl-1H-imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b...
| Autores principales: | , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2016
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273229/ https://www.ncbi.nlm.nih.gov/pubmed/27023499 http://dx.doi.org/10.3390/molecules21040400 |
| _version_ | 1783377336035442688 |
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| author | Boulebd, Houssem Ismaili, Lhassane Bartolini, Manuela Bouraiou, Abdelmalek Andrisano, Vincenza Martin, Helene Bonet, Alexandre Moraleda, Ignacio Iriepa, Isabel Chioua, Mourad Belfaitah, Ali Marco-Contelles, José |
| author_facet | Boulebd, Houssem Ismaili, Lhassane Bartolini, Manuela Bouraiou, Abdelmalek Andrisano, Vincenza Martin, Helene Bonet, Alexandre Moraleda, Ignacio Iriepa, Isabel Chioua, Mourad Belfaitah, Ali Marco-Contelles, José |
| author_sort | Boulebd, Houssem |
| collection | PubMed |
| description | Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized imidazo pyranotacrines as non-hepatotoxic, multipotent tacrine analogues. Among these compounds, 1-(5-amino-2-methyl-4-(1-methyl-1H-imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinolin-3-yl)ethan-1-one (4) is non-hepatotoxic (cell viability assay on HepG2 cells), a selective but moderately potent EeAChE inhibitor (IC(50) = 38.7 ± 1.7 μM), and a very potent antioxidant agent on the basis of the ORAC test (2.31 ± 0.29 μmol·Trolox/μmol compound). |
| format | Online Article Text |
| id | pubmed-6273229 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2016 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-62732292018-12-28 Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy Boulebd, Houssem Ismaili, Lhassane Bartolini, Manuela Bouraiou, Abdelmalek Andrisano, Vincenza Martin, Helene Bonet, Alexandre Moraleda, Ignacio Iriepa, Isabel Chioua, Mourad Belfaitah, Ali Marco-Contelles, José Molecules Article Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized imidazo pyranotacrines as non-hepatotoxic, multipotent tacrine analogues. Among these compounds, 1-(5-amino-2-methyl-4-(1-methyl-1H-imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinolin-3-yl)ethan-1-one (4) is non-hepatotoxic (cell viability assay on HepG2 cells), a selective but moderately potent EeAChE inhibitor (IC(50) = 38.7 ± 1.7 μM), and a very potent antioxidant agent on the basis of the ORAC test (2.31 ± 0.29 μmol·Trolox/μmol compound). MDPI 2016-03-24 /pmc/articles/PMC6273229/ /pubmed/27023499 http://dx.doi.org/10.3390/molecules21040400 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Article Boulebd, Houssem Ismaili, Lhassane Bartolini, Manuela Bouraiou, Abdelmalek Andrisano, Vincenza Martin, Helene Bonet, Alexandre Moraleda, Ignacio Iriepa, Isabel Chioua, Mourad Belfaitah, Ali Marco-Contelles, José Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title | Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title_full | Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title_fullStr | Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title_full_unstemmed | Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title_short | Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy |
| title_sort | imidazopyranotacrines as non-hepatotoxic, selective acetylcholinesterase inhibitors, and antioxidant agents for alzheimer′s disease therapy |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273229/ https://www.ncbi.nlm.nih.gov/pubmed/27023499 http://dx.doi.org/10.3390/molecules21040400 |
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