Synthesis of new ferulic/lipoic/comenic acid-melatonin hybrids as antioxidants and Nrf2 activators via Ugi reaction
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 8e and 8g, showing a potent antioxidant capacity, a remarkable neuroprotective effect against the cell death induced by H2O2 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.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2019 |
|---|---|
| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:11 |
|---|---|
| Enthalten in: |
Future medicinal chemistry - 11(2019), 24 vom: 21. Dez., Seite 3097-3108 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Pachón-Angona, Irene [VerfasserIn] |
|---|
| Links: |
|---|
| Anmerkungen: |
Date Completed 10.07.2020 Date Revised 10.07.2020 published: Print Citation Status MEDLINE |
|---|
| doi: |
10.4155/fmc-2019-0191 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM304399647 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM304399647 | ||
| 003 | DE-627 | ||
| 005 | 20231225114913.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2019 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.4155/fmc-2019-0191 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1014.xml |
| 035 | |a (DE-627)NLM304399647 | ||
| 035 | |a (NLM)31838896 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Pachón-Angona, Irene |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of new ferulic/lipoic/comenic acid-melatonin hybrids as antioxidants and Nrf2 activators via Ugi reaction |
| 264 | 1 | |c 2019 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 10.07.2020 | ||
| 500 | |a Date Revised 10.07.2020 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a 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 8e and 8g, showing a potent antioxidant capacity, a remarkable neuroprotective effect against the cell death induced by H2O2 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a ARE cells | |
| 650 | 4 | |a Nrf2 pathway | |
| 650 | 4 | |a ORAC | |
| 650 | 4 | |a Ugi multicomponent reaction | |
| 650 | 4 | |a antioxidants | |
| 650 | 7 | |a Antioxidants |2 NLM | |
| 650 | 7 | |a Carboxylic Acids |2 NLM | |
| 650 | 7 | |a Coumaric Acids |2 NLM | |
| 650 | 7 | |a NF-E2-Related Factor 2 |2 NLM | |
| 650 | 7 | |a NFE2L2 protein, human |2 NLM | |
| 650 | 7 | |a Neuroprotective Agents |2 NLM | |
| 650 | 7 | |a Pyrones |2 NLM | |
| 650 | 7 | |a comenic acid |2 NLM | |
| 650 | 7 | |a Thioctic Acid |2 NLM | |
| 650 | 7 | |a 73Y7P0K73Y |2 NLM | |
| 650 | 7 | |a ferulic acid |2 NLM | |
| 650 | 7 | |a AVM951ZWST |2 NLM | |
| 650 | 7 | |a Hydrogen Peroxide |2 NLM | |
| 650 | 7 | |a BBX060AN9V |2 NLM | |
| 650 | 7 | |a Melatonin |2 NLM | |
| 650 | 7 | |a JL5DK93RCL |2 NLM | |
| 700 | 1 | |a Martin, Helène |e verfasserin |4 aut | |
| 700 | 1 | |a Chhor, Stecy |e verfasserin |4 aut | |
| 700 | 1 | |a Oset-Gasque, María-Jesús |e verfasserin |4 aut | |
| 700 | 1 | |a Refouvelet, Bernard |e verfasserin |4 aut | |
| 700 | 1 | |a Marco-Contelles, José |e verfasserin |4 aut | |
| 700 | 1 | |a Ismaili, Lhassane |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Future medicinal chemistry |d 2009 |g 11(2019), 24 vom: 21. Dez., Seite 3097-3108 |w (DE-627)NLM194822109 |x 1756-8927 |7 nnns |
| 773 | 1 | 8 | |g volume:11 |g year:2019 |g number:24 |g day:21 |g month:12 |g pages:3097-3108 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.4155/fmc-2019-0191 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 11 |j 2019 |e 24 |b 21 |c 12 |h 3097-3108 | ||