Full Text Journal Articles by
Author Bernard Refouvelet

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Synthesis of Hantzsch Adducts as Cholinesterases and Calcium Flux inhibitors, Antioxidants and Neuroprotectives.

Irene Pachón Angona, Helene Martin, Solene Daniel, Ignacio Moraleda, Alexandre Bonet, Artur Wnorowski, Maciej Maj, Krzysztof Jozwiak, Isabel Iriepa, Bernard Refouvelet, José Marco-Contelles, Lhassane Ismaili,

We report herein the design, synthesis, biological evaluation, and molecular modelling of new inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), able to block Ca+2 channels also showing antioxidant and neuroprotective activities. The new MTDL, dialkyl 2,6-dimethyl-4-(4-((5-aminoalkyl)oxy)phenyl)-1,4-dihydropyridine-3,5-dicarboxylate 3a-p, have been obtained via Hantzsch reaction from appropriate and commercially available precursors. Pertinent ... Read more >>

Int J Mol Sci (International journal of molecular sciences)
[2020, 21(20):]

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Acetylcholinesterase Inhibition of Diversely Functionalized Quinolinones for Alzheimer's Disease Therapy.

Óscar M Bautista-Aguilera, Lhassane Ismaili, Mourad Chioua, Rudolf Andrys, Monika Schmidt, Petr Bzonek, María Ángeles Martínez-Grau, Christopher D Beadle, Tatiana Vetman, Francisco López-Muñoz, Isabel Iriepa, Bernard Refouvelet, Kamil Musilek, José Marco-Contelles,

In this communication, we report the synthesis and cholinesterase (ChE)/monoamine oxidase (MAO) inhibition of 19 quinolinones (QN1-19) and 13 dihydroquinolinones (DQN1-13) designed as potential multitarget small molecules (MSM) for Alzheimer's disease therapy. Contrary to our expectations, none of them showed significant human recombinant MAO inhibition, but compounds QN8, QN9, and ... Read more >>

Int J Mol Sci (International journal of molecular sciences)
[2020, 21(11):]

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Design, Synthesis and Biological Evaluation of New Antioxidant and Neuroprotective Multitarget Directed Ligands Able to Block Calcium Channels.

Irene Pachòn Angona, Solene Daniel, Helene Martin, Alexandre Bonet, Artur Wnorowski, Maciej Maj, Krzysztof Jóźwiak, Tiago Barros Silva, Bernard Refouvelet, Fernanda Borges, José Marco-Contelles, Lhassane Ismaili,

We report herein the design, synthesis and biological evaluation of new antioxidant and neuroprotective multitarget directed ligands (MTDLs) able to block Ca2+ channels. New dialkyl 2,6-dimethyl-4-(4-(prop-2-yn-1-yloxy)phenyl)-1,4-dihydropyridine-3,5-dicarboxylate MTDLs 3a-t, resulting from the juxtaposition of nimodipine, a Ca2+ channel antagonist, and rasagiline, a known MAO inhibitor, have been obtained from appropriate and ... Read more >>

Molecules (Molecules (Basel, Switzerland))
[2020, 25(6):]

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Synthesis of new ferulic/lipoic/comenic acid-melatonin hybrids as antioxidants and Nrf2 activators via Ugi reaction.

Irene Pachón-Angona, Helène Martin, Stecy Chhor, María-Jesús Oset-Gasque, Bernard Refouvelet, José Marco-Contelles, Lhassane Ismaili,

Aim: Oxidative stress has been implicated in the pathogenesis of many neurodegenerative diseases, and particularly in Alzheimer's disease. Results: This work describes the Ugi multicomponent synthesis, antioxidant power and Nrf2 pathway induction in antioxidant response element cells of (E)-N-(2-((2-(1H-indol-3-yl)ethyl)amino)-2-oxoethyl)-N-(2-(5-(benzyloxy)-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acryl amides 8a-d, N-(2-((2-(1H-indol-3-yl)ethyl)amino)-2-oxoethyl)-N-(2-(5-(benzyloxy)-1H-indol-3-yl)ethyl)-5-(1,2-dithiolan-3-yl)pentanamides 8e-h and N-(2-((2-(1H-indol-3-yl)ethyl)amino)-2-oxoethyl)-N-(2-(5-(benzyloxy)-1H-indol-3-yl)ethyl)-5-hydroxy-4-oxo-4H-pyran-2-carboxamides 8i,j. Conclusion: We have identified compounds ... Read more >>

Future Med Chem (Future medicinal chemistry)
[2019, 11(24):3097-3108]

Cited: 1 time

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Donepezil + chromone + melatonin hybrids as promising agents for Alzheimer's disease therapy.

Irene Pachón-Angona, Bernard Refouvelet, Rudolf Andrýs, Helène Martin, Vincent Luzet, Isabel Iriepa, Ignacio Moraleda, Daniel Diez-Iriepa, María-Jesús Oset-Gasque, José Marco-Contelles, Kamil Musilek, Lhassane Ismaili,

We describe herein the design, multicomponent synthesis and biological studies of new donepezil + chromone + melatonin hybrids as potential agents for Alzheimer's disease (AD) therapy. We have identified compound 14n as promising multitarget small molecule showing strong BuChE inhibition (IC50 = 11.90 ± 0.05 nM), moderate hAChE (IC50 = 1.73 ± 0.34 μM), hMAO A (IC50 = 2.78 ± 0.12 μM), and MAO B (IC50 = 21.29 ± 3.85 μM) inhibition, while keeping ... Read more >>

J Enzyme Inhib Med Chem (Journal of enzyme inhibition and medicinal chemistry)
[2019, 34(1):479-489]

Cited: 3 times

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Synthesis and biological assessment of KojoTacrines as new agents for Alzheimer's disease therapy.

Youssef Dgachi, Hélène Martin, Rim Malek, Daniel Jun, Jana Janockova, Vendula Sepsova, Ondrej Soukup, Isabel Iriepa, Ignacio Moraleda, Emna Maalej, M Carmo Carreiras, Bernard Refouvelet, Fakher Chabchoub, José Marco-Contelles, Lhassane Ismaili,

In view of the multifactorial nature of Alzheimer's disease (AD), multitarget small molecules (MTSM) represent the most potent and attractive therapeutic strategy to design new drugs for Alzheimer's disease therapy. The new MTSM KojoTacrines (KTs) were designed and synthesized by juxtaposition of selected pharmacophoric motifs from kojic acid and tacrine. ... Read more >>

J Enzyme Inhib Med Chem (Journal of enzyme inhibition and medicinal chemistry)
[2019, 34(1):163-170]

Cited: 1 time

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Synthesis and Biological Evaluation of Novel Chromone+Donepezil Hybrids for Alzheimer's Disease Therapy.

Rim Malek, Bernard Refouvelet, Mohamed Benchekroun, Isabel Iriepa, Ignacio Moraleda, Rudolf Andrys, Kamil Musilek, José Marco-Contelles, Lhassane Ismaili,

BACKGROUND:Many factors are involved in Alzheimer's Disease (AD) such as amyloid plaques, neurofibrillary tangles, cholinergic deficit and oxidative stress. To counter the complexity of the disease the new approach for drug development is to create a single molecule able to act simultaneously on different targets. OBJECTIVE:We conceived eight drug likeliness ... Read more >>

Curr Alzheimer Res (Current Alzheimer research)
[2019, 16(9):815-820]

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The Antioxidant Additive Approach for Alzheimer's Disease Therapy: New Ferulic (Lipoic) Acid Plus Melatonin Modified Tacrines as Cholinesterases Inhibitors, Direct Antioxidants, and Nuclear Factor (Erythroid-Derived 2)-Like 2 Activators.

Mohamed Benchekroun, Alejandro Romero, Javier Egea, Rafael León, Patrycja Michalska, Izaskun Buendía, María Luisa Jimeno, Daniel Jun, Jana Janockova, Vendula Sepsova, Ondrej Soukup, Oscar M Bautista-Aguilera, Bernard Refouvelet, Olivier Ouari, José Marco-Contelles, Lhassane Ismaili,

Novel multifunctional tacrines for Alzheimer's disease were obtained by Ugi-reaction between ferulic (or lipoic acid), a melatonin-like isocyanide, formaldehyde, and tacrine derivatives, according to the antioxidant additive approach in order to modulate the oxidative stress as therapeutic strategy. Compound 5c has been identified as a promising permeable agent showing excellent ... Read more >>

J. Med. Chem. (Journal of medicinal chemistry)
[2016, 59(21):9967-9973]

Cited: 13 times

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Multitarget compounds bearing tacrine- and donepezil-like structural and functional motifs for the potential treatment of Alzheimer's disease.

Lhassane Ismaili, Bernard Refouvelet, Mohamed Benchekroun, Simone Brogi, Margherita Brindisi, Sandra Gemma, Giuseppe Campiani, Slavica Filipic, Danica Agbaba, Gerard Esteban, Mercedes Unzeta, Katarina Nikolic, Stefania Butini, José Marco-Contelles,

Alzheimer's disease is a multifactorial and fatal neurodegenerative disorder characterized by decline of cholinergic function, deregulation of other neurotransmitter systems, β-amyloid fibril deposition, and β-amyloid oligomers formation. Based on the involvement of a relevant number of biological systems in Alzheimer's disease progression, multitarget compounds may enable therapeutic efficacy. Accordingly, compounds ... Read more >>

Prog Neurobiol (Progress in neurobiology)
[2017, 151:4-34]

Cited: 21 times

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Donepezil-ferulic acid hybrids as anti-Alzheimer drugs.

Mohamed Benchekroun, Lhassane Ismaili, Marc Pudlo, Vincent Luzet, Tijani Gharbi, Bernard Refouvelet, José Marco-Contelles,

BACKGROUND: Due to the complex nature of Alzheimer's disease, there is a renewed and growing search for multitarget drugs. RESULTS: Donepezil-ferulic acid hybrids (DFAHs) were prepared by the one-pot Ugi-4CR in low-to-moderate yields. DFAHs are potent antioxidant agents, showing oxygen radical absorbance capacity values in the range 4.80-8.71 trolox equivalents, ... Read more >>

Future Med Chem (Future medicinal chemistry)
[2015, 7(1):15-21]

Cited: 10 times

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Novel tacrine-grafted Ugi adducts as multipotent anti-Alzheimer drugs: a synthetic renewal in tacrine-ferulic acid hybrids.

Mohamed Benchekroun, Manuela Bartolini, Javier Egea, Alejandro Romero, Elena Soriano, Marc Pudlo, Vincent Luzet, Vincenza Andrisano, María-Luisa Jimeno, Manuela G López, Sarah Wehle, Tijani Gharbi, Bernard Refouvelet, Lucía de Andrés, Clara Herrera-Arozamena, Barbara Monti, Maria Laura Bolognesi, María Isabel Rodríguez-Franco, Michael Decker, José Marco-Contelles, Lhassane Ismaili,

Herein we describe the design, multicomponent synthesis, and biological, molecular modeling and ADMET studies, as well as in vitro PAMPA-blood-brain barrier (BBB) analysis of new tacrine-ferulic acid hybrids (TFAHs). We identified (E)-3-(hydroxy-3-methoxyphenyl)-N-{8[(7-methoxy-1,2,3,4-tetrahydroacridin-9-yl)amino]octyl}-N-[2-(naphthalen-2-ylamino)2-oxoethyl]acrylamide (TFAH 10 n) as a particularly interesting multipotent compound that shows moderate and completely selective inhibition of human butyrylcholinesterase ... Read more >>

ChemMedChem (ChemMedChem)
[2015, 10(3):523-539]

Cited: 20 times

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Quinolone-benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer disease.

Marc Pudlo, Vincent Luzet, Lhassane Ismaïli, Isabelle Tomassoli, Anne Iutzeler, Bernard Refouvelet,

Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high ... Read more >>

Bioorg. Med. Chem. (Bioorganic & medicinal chemistry)
[2014, 22(8):2496-2507]

Cited: 11 times

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Pharmacophore modelling and synthesis of quinoline-3-carbohydrazide as antioxidants.

Mustapha El Bakkali, Lhassane Ismaili, Isabelle Tomassoli, Laurence Nicod, Marc Pudlo, Bernard Refouvelet,

From well-known antioxidants agents, we developed a first pharmacophore model containing four common chemical features: one aromatic ring and three hydrogen bond acceptors. This model served as a template in virtual screening of Maybridge and NCI databases that resulted in selection of sixteen compounds. The selected compounds showed a good ... Read more >>

(International journal of medicinal chemistry)
[2011, 2011:592879]

Cited: 1 time

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Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists.

Isabelle Tomassoli, Lhassane Ismaili, Marc Pudlo, Cristóbal de Los Ríos, Elena Soriano, Inés Colmena, Luis Gandía, Luis Rivas, Abdelouahid Samadi, José Marco-Contelles, Bernard Refouvelet,

The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c]quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved ... Read more >>

Eur J Med Chem (European journal of medicinal chemistry)
[2011, 46(1):1-10]

Cited: 18 times

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Synthesis and antioxidant activity evaluation of new hexahydropyrimido[5,4-c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4-c]quinoline-5-ones obtained by Biginelli reaction in two steps.

Lhassane Ismaili, Arulraj Nadaradjane, Laurence Nicod, Catherine Guyon, Alain Xicluna, Jean-François Robert, Bernard Refouvelet,

New hexahydropyrimido[5,4-c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4-c]quinoline-5-ones were prepared in two steps from ethyl 4-phenyl-6-methyl-2-oxo tetrahydropyrimidine-5-carboxylates or 4-phenyl-6-methyl-2-thioxotetrahydropyrimidine-5-carboxylates, previously prepared by Biginelli reaction using appropriate aldehyde, urea derivatives and ethyl acetoacetate. Their antioxidant properties were evaluated by two methods: scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and scavenging effect on hydroxyl radicals. The results ... Read more >>

Eur J Med Chem (European journal of medicinal chemistry)
[2008, 43(6):1270-1275]

Cited: 10 times

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A novel cyclic hexapeptide as chiral selector: Application for HPLC separation of a series of dansyl amino and arylalkanoic acids.

Claire André, Mireille Thomassin, Arunalyat Umrayami, Lhassane Ismaili, Bernard Refouvelet, Yves-Claude Guillaume,

In this paper, the synthesis of a cyclic hexapeptide molecule was presented and evaluated for the enantiomer separation of a series of dansyl amino and arylalkanoic acids using high performance liquid chromatography (HPLC). It was clearly vizualized that this chiral selector allowed the separation of a great number of enantiomer ... Read more >>

Talanta (Talanta)
[2007, 71(4):1817-1823]

Cited: 0 times

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Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells.

Yves Jacquot, Ioanna Laïos, Anny Cleeren, Denis Nonclercq, Laurent Bermont, Bernard Refouvelet, Kamal Boubekeur, Alain Xicluna, Guy Leclercq, Guy Laurent,

A number of coumarins exhibit interesting pharmacological activities and are therefore of therapeutic use. We report here the synthesis and the structural analysis of new N-substituted 4-amino-3-(2-methylbenzyl)coumarins (compounds 8a-8e) that present structural analogies with estrothiazine and 11- or 7-substituted 17beta-estradiol. These derivatives were tested with respect to estrogenic activity on ... Read more >>

Bioorg. Med. Chem. (Bioorganic & medicinal chemistry)
[2007, 15(6):2269-2282]

Cited: 11 times

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Synthesis of 4-hydroxycoumarin and 2,4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture.

Bernard Refouvelet, Catherine Guyon, Yves Jacquot, Corinne Girard, Hervé Fein, Françoise Bévalot, Jean-François Robert, Bruno Heyd, Georges Mantion, Lysiane Richert, Alain Xicluna,

We report here the synthesis of aromatic coumarins and aromatic alpha-quinolones which were evaluated in vitro for their protective potentialities against tert-butyl hydroperoxide (t-BHP)-induced oxidative damage on human liver cell death, i.e., human hepatoma HepG2 cell line and human hepatocytes in primary culture. We found that the presence of a ... Read more >>

Eur J Med Chem (European journal of medicinal chemistry)
[2004, 39(11):931-937]

Cited: 7 times

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Concentration of sodium ion as the determining factor for the association of dansyl amino acids with the teicoplanin molecule in reversed-phase liquid chromatography.

Lhassane Ismaili, Tong Than Truong, Claire André, Mireille Thomassin, Jean-Louis Mozer, Jean-Francois Robert, Alain Xicluna, Bernard Refouvelet, Joelle Millet, Laurence Nicod, Yves-Claude Guillaume,

The mechanism of the binding of D,L dansyl amino acids to teicoplanin was investigated. Na+ was used as an indicator of the interactions between the solutes and teicoplanin. The number (n) of sodium ions, Na+, excluded from the solute-teicoplanin interface when analyte transfer occurred was determined. A thermodynamic study and ... Read more >>

J AOAC Int (Journal of AOAC International)
[2003, 86(2):222-228]

Cited: 2 times

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Method for preparing 13 5-triaminobenzene and hydrolyzing it into high-purity phloroglucinal

LHASSANE ISMAILI, BERNARD REFOUVELET, ALAIN XICLUNA,

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Cited: 0 times

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Pharmacological profile of 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b] [1,4]benzothiazin-6-one, a novel human estrogen receptor agonist.

Yves Jacquot, Anny Cleeren, Ioanna Laios, Ma Yan, Athem Boulahdour, Laurent Bermont, Bernard Refouvelet, Gérard Adessi, Guy Leclercq, Alain Xicluna,

Pharmacological studies were carried out to characterize further the endocrinological profile and the binding mode to the estrogen receptor (ER) of 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one (1). Binding experiments were conducted with highly purified recombinant human estrogen receptors hERa and beta. Potent estrogenic activity of compound 1 was assessed by testing its ability to ... Read more >>

Biol. Pharm. Bull. (Biological & pharmaceutical bulletin)
[2002, 25(3):335-341]

Cited: 7 times

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