Tetrahydropyranodiquinolin-8-amines as new, non hepatotoxic, antioxidant, and acetylcholinesterase inhibitors for Alzheimer's disease therapy

Dgachi, Youssef; Sokolov, Olga; Luzet, Vincent; Godyń, Justyna; Panek, Dawid; Bonet, Alexandre; Martin, Hélène; Iriepa, Isabel; Moraleda, Ignacio; García‐Iriepa, Cristina; Janočková, Jana; Richert, Lysiane; Soukup, Ondřej; Malawska, Barbara; Chabchoub, Fakher; Marco‐Contelles, José; Ismaïli, Lhassane

doi:10.1016/j.ejmech.2016.11.050

Cited by 38 publications

(23 citation statements)

References 45 publications

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“…The great interest of the cyclization processes is based on the fact that the pyrano[3,2‐ h ]quinoline scaffold presents: a) antiproliferative and antioxidant activities useful in the treatment of the Alzheimer's disease and b) promising metal‐chelating properties.…”

Section: Resultsmentioning

confidence: 99%

Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O‐Propargyl‐2‐aminophenols

et al. 2018

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A fruitful divergent cyclization of terminal alkynes arising from 2‐aminophenols depending on the transition metal employed is reported. Under palladium‐ and platinum‐catalysis, the total regioselective carbon–nitrogen or carbon–carbon bonds formation afforded 1,4‐benzoxazines or benzopyrans, through different reaction pathways. The subsequent functionalization of the benzopyran scaffold paved the way for a new synthesis of the tricyclic pyrano[3,2‐h]quinolines.

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Section: Resultsmentioning

confidence: 99%

Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O‐Propargyl‐2‐aminophenols

et al. 2018

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“…In this sense, a wide range of molecules has been developed, focusing on possible multitarget drugs for the treatment of AD and other NDDs. Among these drugs, there may be highlighted the molecules derived from various compounds, as triazole (TRI) ( 16 ) [164,165,166,167,168,169] diferiprone (DFP) ( 17 ) [170,171,172,173], 8-hydroxyquinoline (8-HQ) ( 18 ) [163,174,175,176,177,178], cyclam (CY) ( 19 ) [179,180,181,182,183], thioflavine T (ThT) ( 20 ) [19,184,185,186,187], p -I-stilbene (pISTIB) ( 21 ) [188,189,190,191,192,193,194,195,196], chalcone (CHAL) ( 22 ) [167,168], resveratrol (RESV) ( 23 ) [197,198], flavone (FLAV) ( 24 ) [199,200], donepezil (DONE) ( 25 ) [201,202,203,204,205], tacrine (TAC) ( 26 ) [206,207,208,209,210,211,212,213,214,215,216,217,218,219], dopamine (DOP) ( 27 ) [220] and peptide-based inhibitors (PEP) [221,…”

Section: Chelating Agentsmentioning

confidence: 99%

Recent Developments in Metal-Based Drugs and Chelating Agents for Neurodegenerative Diseases Treatments

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Castro

et al. 2019

IJMS

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The brain has a unique biological complexity and is responsible for important functions in the human body, such as the command of cognitive and motor functions. Disruptive disorders that affect this organ, e.g. neurodegenerative diseases (NDDs), can lead to permanent damage, impairing the patients’ quality of life and even causing death. In spite of their clinical diversity, these NDDs share common characteristics, such as the accumulation of specific proteins in the cells, the compromise of the metal ion homeostasis in the brain, among others. Despite considerable advances in understanding the mechanisms of these diseases and advances in the development of treatments, these disorders remain uncured. Considering the diversity of mechanisms that act in NDDs, a wide range of compounds have been developed to act by different means. Thus, promising compounds with contrasting properties, such as chelating agents and metal-based drugs have been proposed to act on different molecular targets as well as to contribute to the same goal, which is the treatment of NDDs. This review seeks to discuss the different roles and recent developments of metal-based drugs, such as metal complexes and metal chelating agents as a proposal for the treatment of NDDs.

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“…Besides well-known antioxidants, phenolic compounds, a number of other class compounds have been identified as possessing antioxidant activity. Thiol- [11] and amine-containing [12] compounds are among them, making different heterocycles attractive scaffolds for the development of new antioxidant agents. Derivatives bearing 1,3,4-thiadiazole [13] and pyrazole [14,15] moieties have been recently demonstrated to possess antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity

et al. 2019

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A series of novel 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives containing chloro, hydroxyl, isopropyl, nitro, nitroso, and amino substituents at benzene ring and 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carbohydrazide derivatives bearing heterocyclic moieties were synthesized. Antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method and reducing power assay. A number of compounds were identified as potent antioxidants. Antioxidant activity of 1-(5-chloro-2-hydroxyphenyl)-4-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrrolidin-2-one has been tested to be 1.5 times higher than that of a well-known antioxidant ascorbic acid. 1-(5-Chloro-2-hydroxyphenyl)-4-(4-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-one has shown 1.35 times higher antioxidant activity than that of vitamin C by DPPH radical scavenging method and optical density value of 1.149 in reducing power assay. The structure of 1-(5-chloro-2-hydroxyphenyl)-N-(1,3-dioxoisoindolin-2-yl)-5-oxopyrrolidine-3-carboxamide was unambiguously assigned by means of X-ray diffraction analysis data.

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Tetrahydropyranodiquinolin-8-amines as new, non hepatotoxic, antioxidant, and acetylcholinesterase inhibitors for Alzheimer's disease therapy

Cited by 38 publications

References 45 publications

Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O‐Propargyl‐2‐aminophenols

Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O‐Propargyl‐2‐aminophenols

Recent Developments in Metal-Based Drugs and Chelating Agents for Neurodegenerative Diseases Treatments

Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity

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