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

Abstract : 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-(1 H-indol-3-yl)ethyl)amino)-2-oxoethyl)- N-(2-(5-(benzyloxy)-1 H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acryl amides 8a–d, N-(2-((2-(1 H-indol-3-yl)ethyl)amino)-2-oxoethyl)- N-(2-(5-(benzyloxy)-1 H-indol-3-yl)ethyl)-5-(1,2-dithiolan-3-yl)pentanamides 8e–h and N-(2-((2-(1 H-indol-3-yl)ethyl)amino)-2-oxoethyl)- N-(2-(5-(benzyloxy)-1 H-indol-3-yl)ethyl)-5-hydroxy-4-oxo-4 H-pyran-2-carboxamides 8i,j. Conclusion: We have identified compounds 8e and 8g, showing a potent antioxidant capacity, a remarkable neuroprotective effect against the cell death induced by H 2 O 2 in SH-SY5Y cells, and a performing activation of the Nrf2 signaling pathway, as very interesting new antioxidant agents for pathologies that curse with oxidative stress.
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https://hal-univ-fcomte.archives-ouvertes.fr/hal-03654634
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Submitted on : Thursday, April 28, 2022 - 5:08:48 PM
Last modification on : Friday, April 29, 2022 - 3:08:36 AM

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Irene Pachón-Angona, Helène Martin, Stecy Chhor, María-Jesús Oset-Gasque, Bernard Refouvelet, et al.. Synthesis of new ferulic/lipoic/comenic acid-melatonin hybrids as antioxidants and Nrf2 activators via Ugi reaction. Future Medicinal Chemistry, Future Science, 2019, 11 (24), pp.3097-3108. ⟨10.4155/fmc-2019-0191⟩. ⟨hal-03654634⟩

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