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Article

Efficient Two-Step Synthesis of Novel Pyrimido[4,5-d] Pyrimidines with Potent Neuroprotective, Antioxidant, and Aβ Anti-Aggregation Properties

by
Ghada Ben Ameur
1,
Emna Maalej
2,
Helene Martin
3,
Anne-Sophie Jacquinot
3,
Nadine Barbanneau
4,
Paul J. Bernard
4,
José Marco-Contelles
5,6,
Fakher Chabchoub
1,* and
Lhassane Ismaili
4,*
1
Laboratory of Applied Chemistry, Heterocycles, Lipids and Polymers, Faculty of Sciences of Sfax, University of Sfax, B.P. 802, Sfax 3000, Tunisia
2
Laboratoire Matériaux, Traitement et Analyse (LMTA), Institut National de Recherche et d’Analyse Physico-Chimique (INRAP), Ariana 2020, Tunisia
3
Université de Franche-Comté, EFS, INSERM, UMR RIGHT, F-25000 Besançon, France
4
Université de Franche-Comté, UMR INSERM 1322 LINC, F-25000 Besançon, France
5
Laboratory of Medicinal Chemistry (IQOG, CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain
6
Center for Biomedical Network Research on Rare Diseases (CIBERER), CIBER, ISCIII, 28006 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Chemistry 2024, 6(4), 695-705; https://doi.org/10.3390/chemistry6040041
Submission received: 18 July 2024 / Revised: 1 August 2024 / Accepted: 2 August 2024 / Published: 7 August 2024
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Eleven new differently substituted N,7-diphenylpyrimido [4,5-d]pyrimidin-4-amines 4a–k were synthesized from readily available reagents in a simple and inexpensive two-step procedure with yields up to 57%. Neuroprotective analysis against H2O2 and analysis using ORAC assays identified compounds 4g, 4i and 4j as promising antioxidant compounds. These compounds also showed potent inhibition of Aβ1–42 self-aggregation, and suitable physicochemical properties predicted by Datawarior software V6.1.0, this biological activity and physicochemical property being of great interest for pathologies linked to oxidative stress, such as Alzheimer’s disease.
Keywords: Aβ1-42 self-aggregation inhibition; antioxidant; neuroprotective agents; pyrimido [4,5-d] pyrimidines Aβ1-42 self-aggregation inhibition; antioxidant; neuroprotective agents; pyrimido [4,5-d] pyrimidines

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MDPI and ACS Style

Ben Ameur, G.; Maalej, E.; Martin, H.; Jacquinot, A.-S.; Barbanneau, N.; Bernard, P.J.; Marco-Contelles, J.; Chabchoub, F.; Ismaili, L. Efficient Two-Step Synthesis of Novel Pyrimido[4,5-d] Pyrimidines with Potent Neuroprotective, Antioxidant, and Aβ Anti-Aggregation Properties. Chemistry 2024, 6, 695-705. https://doi.org/10.3390/chemistry6040041

AMA Style

Ben Ameur G, Maalej E, Martin H, Jacquinot A-S, Barbanneau N, Bernard PJ, Marco-Contelles J, Chabchoub F, Ismaili L. Efficient Two-Step Synthesis of Novel Pyrimido[4,5-d] Pyrimidines with Potent Neuroprotective, Antioxidant, and Aβ Anti-Aggregation Properties. Chemistry. 2024; 6(4):695-705. https://doi.org/10.3390/chemistry6040041

Chicago/Turabian Style

Ben Ameur, Ghada, Emna Maalej, Helene Martin, Anne-Sophie Jacquinot, Nadine Barbanneau, Paul J. Bernard, José Marco-Contelles, Fakher Chabchoub, and Lhassane Ismaili. 2024. "Efficient Two-Step Synthesis of Novel Pyrimido[4,5-d] Pyrimidines with Potent Neuroprotective, Antioxidant, and Aβ Anti-Aggregation Properties" Chemistry 6, no. 4: 695-705. https://doi.org/10.3390/chemistry6040041

APA Style

Ben Ameur, G., Maalej, E., Martin, H., Jacquinot, A.-S., Barbanneau, N., Bernard, P. J., Marco-Contelles, J., Chabchoub, F., & Ismaili, L. (2024). Efficient Two-Step Synthesis of Novel Pyrimido[4,5-d] Pyrimidines with Potent Neuroprotective, Antioxidant, and Aβ Anti-Aggregation Properties. Chemistry, 6(4), 695-705. https://doi.org/10.3390/chemistry6040041

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