Synthesis, antioxidant and Aβ anti-aggregation properties of new ferulic, caffeic and lipoic acid derivatives obtained by the Ugi four-component reaction

被引：21

作者：

Benchekroun, Mohamed ^{[1
,5
]}

Pachon-Angona, Irene ^{[1
]}

Luzet, Vincent ^{[1
]}

Martin, Helene ^{[2
]}

Oset-Gasque, Maria-Jesus ^{[3
]}

Marco-Contelles, Jose ^{[4
]}

Ismaili, Lhassane ^{[1
]}

机构：

[1] Univ Bourgogne Franche Comte, Pole Chim Organ & Therapeut, Lab Neurosci Integrat & Clin EA 481, UFR Sante, 19 Rue Ambroise Pare, F-25000 Besancon, France

[2] Univ Bourgogne Franche Comte, Lab Toxicol Cellulaire, PEPITE EA4267, F-25000 Besancon, France

[3] Univ Complutense Madrid, Fac Pharm, Dept Biochem & Mol Biol, Madrid 28040, Spain

[4] CSIC, Lab Med Chem, IQOG, Juan Cierva 3, E-28006 Madrid, Spain

[5] CNRS, Inst Chim Subst Nat, Ctr Rech Gif Sur Yvette, UPR 2301, Ave Terrasse, F-91198 Gif Sur Yvette, France

来源：

BIOORGANIC CHEMISTRY | 2019年 / 85卷

关键词：

A beta(1-40) self-aggregation inhibition; Antioxidants; Benzylamine; Benzyl isocyanide; Caffeic acid; Ferulic acid; (R)-Lipoic acid; Multicomponent reactions; Ugi four-component reaction; ALZHEIMERS-DISEASE; BIOLOGICAL ASSESSMENT; MULTICOMPONENT; INHIBITORS; CHEMISTRY;

D O I：

10.1016/j.bioorg.2018.12.029

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We report herein the synthesis antioxidant and A beta anti-aggregation capacity of (E)-N-benzyl-N-[2-(benzyla-mino)-2-oxoethyl]-3-(aryl)acrylamides and related (R)-N-benzyl-N-(2 (benzylamino)-2-oxoethyl)-5-(1,2-dithiolan-3-yl)pentanamides 1-12. These compounds have been obtained, via Ugi four-component reaction, from modest to good yields. Their antioxidant analysis, using the DPPH and ORAC assays, allowed us to identify compounds 8 and 9, as potent antioxidant agents, showing also strong A beta(1-40 )self-aggregation inhibition, two biological properties of interest in pathologies linked to the oxidative stress, such as Alzheimer's disease.

引用

页码：221 / 228

页数：8

共 27 条

[1] Isocyanide-based multicomponent reactions in drug discovery [J].

Akritopoulou-Zanze, Irini .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2008, 12 (03) :324-331

[2] Small-molecule inhibitors/modulators of amyloid-β peptide aggregation and toxicity for the treatment of Alzheimer's disease: a patent review (2010-2012) [J].

Belluti, Federica ;

Rampa, Angela ;

Gobbi, Silvia ;

Bisi, Alessandra .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (05) :581-596

[3] 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 [J].

Benchekroun, Mohamed ;

Romero, Alejandro ;

Egea, Javier ;

Leon, Rafael ;

Michalska, Patrycja ;

Buendia, Izaskun ;

Jimeno, Maria Luisa ;

Jun, Daniel ;

Janockova, Jana ;

Sepsova, Vendula ;

Soukup, Ondrej ;

Bautista-Aguilera, Oscar M. ;

Refouvelet, Bernard ;

Ouari, Olivier ;

Marco-Contelles, Jose ;

Ismaili, Lhassane .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (21) :9967-9973

[4]

Benchekroun M, 2015, FUTURE MED CHEM, V7, P15, DOI [10.4155/fmc.14.148, 10.4155/FMC.14.148]

[5] Recent advances in multicomponent reactions for diversity-oriented synthesis [J].

Biggs-Houck, James E. ;

Younai, Ashkaan ;

Shaw, Jared T. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :371-382

[6] α-Aryl-N-alkyl Nitrones, as Potential Agents for Stroke Treatment: Synthesis, Theoretical Calculations, Antioxidant, Anti-inflammatory, Neuroprotective, and Brain-Blood Barrier Permeability Properties [J].

Chioua, Mourad ;

Sucunza, David ;

Soriano, Elena ;

Hadjipavlou-Litina, Dimitra ;

Alcazar, Alberto ;

Ayuso, Irene ;

Jesus Oset-Gasque, Maria ;

Pilar Gonzalez, Maria ;

Monjas, Leticia ;

Isabel Rodriguez-Franco, Maria ;

Marco-Contelles, Jose ;

Samadi, Abdelouahid .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (01) :153-168

[7] Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer Properties [J].

Dai, Jin ;

Mumper, Russell J. .

MOLECULES, 2010, 15 (10) :7313-7352

[8] Extending applicability of the oxygen radical absorbance capacity (ORAC-fluorescein) assay [J].

Dávalos, A ;

Gómez-Cordovés, C ;

Bartolomé, B .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (01) :48-54

[9] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

[10]

HATANO T, 1988, CHEM PHARM BULL, V36, P2090

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