Design, synthesis and evaluation of dihydropyranoindole derivatives as potential cholinesterase inhibitors against Alzheimer’s disease

Shaikh, Sarfaraz; Pavale, Ganesh; Dhavan, Pratik P.; Singh, Pinky; Uparkar, Jasmin; Vaidya, Shashikant; Jadhav, B. L.; Ramana, M. M. V.

doi:10.1016/j.bioorg.2021.104770

Cited by 18 publications

(7 citation statements)

References 40 publications

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“…Based on this classification, 3 (IC 50 = 10.1 µM) and 4 (IC 50 = 10.7 µM) are highly potent AChE inhibitors. The potencies of 3 and 4 were ~ 5 times lower or ~ 2 times higher than that of galantamine [IC 50 values = 2.16 µM 46 or 21.1 µM (6.07 µg/ml) 47 ], which is a natural compound and used for the treatment of AD. Polyphenols that target AChE have attracted research interest as potential therapeutics for AD 48 .…”

Section: Discussionmentioning

confidence: 99%

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Jang

Kang

et al. 2021

Sci Rep

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Among 276 herbal extracts, a methanol extract of Castanopsis cuspidata var. sieboldii stems was selected as an experimental source for novel acetylcholinesterase (AChE) inhibitors. Five compounds were isolated from the extract by activity-guided screening, and their inhibitory activities against butyrylcholinesterase (BChE), monoamine oxidases (MAOs), and β-site amyloid precursor protein cleaving enzyme 1 (BACE-1) were also evaluated. Of these compounds, 4′-O-(α-l-rhamnopyranosyl)-3,3′,4-tri-O-methylellagic acid (3) and 3,3′,4-tri-O-methylellagic acid (4) effectively inhibited AChE with IC50 values of 10.1 and 10.7 µM, respectively. Ellagic acid (5) inhibited AChE (IC50 = 41.7 µM) less than 3 and 4. In addition, 3 effectively inhibited MAO-B (IC50 = 7.27 µM) followed by 5 (IC50 = 9.21 µM). All five compounds weakly inhibited BChE and BACE-1. Compounds 3, 4, and 5 reversibly and competitively inhibited AChE, and were slightly or non-toxic to MDCK cells. The binding energies of 3 and 4 (− 8.5 and − 9.2 kcal/mol, respectively) for AChE were greater than that of 5 (− 8.3 kcal/mol), and 3 and 4 formed a hydrogen bond with Tyr124 in AChE. These results suggest 3 is a dual-targeting inhibitor of AChE and MAO-B, and that these compounds should be viewed as potential therapeutics for the treatment of Alzheimer’s disease.

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Section: Discussionmentioning

confidence: 99%

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Jang

Kang

et al. 2021

Sci Rep

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“…11,12 Molecules with chromenes or pyran-annulated backbones as O-heterocycles demonstrate vast applications in the biological and clinical domain. 4H-chromenes, both natural and synthetic category, exhibit a broad therapeutic potential in the treatment of diverse diseases [13][14][15][16] and distributed throughout the nature with a wide range of remarkable biological properties. [17][18][19][20] Compounds with spirocyclic unit are existent in a wide number of natural products and drug targets.…”

Section: Introductionmentioning

confidence: 99%

Facile one‐pot three‐component route to an assembly of 2‐amino‐4H‐chromenes and spirochromenes promoted via ceria nanoparticles in a benign manner

Khorshidi

Heydari

Maghsoodlou

et al. 2022

Bulletin Korean Chem Soc

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In this study, a series of 2-amino-4H-chromenes and spirochromenes were elaborated and synthesized via a new sustainable one-pot three-component strategy from easily available materials including phloroglucinol, malononitrile, and aldehydes/isatins. Ceria nanoparticles (CeO 2 NPs) were successfully applied as an effective catalyst that recycled and reused with a marginal decrement in its catalytic performance. The Lewis acid-base nature of the described nanocatalyst afforded the high yields of target products. The reaction is run in ethanol as a green solvent to create an environment-friendly process. The other salient merits of this methodology are a broad substrate scope, a simple operation, shorter reaction times, and no need for column chromatographic purification. K E Y W O R D S2-amino-4H-chromenes, CeO 2 NPs, one pot, spirochromenes, three component

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“…[ 10,11 ] 4 H ‐Chromenes are very effective in treating some diseases such as Schizophrenia, [ 12 ] Parkinson's, Down's syndrome, Huntington's, amyotrophic lateral sclerosis, [ 13,14 ] cancer, [ 15 ] and HIV. [ 16 ] In addition, the biomedical applications of indole, 4 H ‐chromene, and sulphonamide are used to make anti‐Alzheimer's drugs. [ 17 ] These molecules are found in nature with many biological properties such as antimicrobial, antiviral, and antioxidant.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐amino‐4H‐chromenes and spirochromenes using basic ionic liquid, 2‐hydroxyethylammonium formate as green, stable, and reusable catalyst

Tazeh

Heydari

Fatahpour

2022

J Chinese Chemical Soc

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In this study, a number of 2-amino-4H-chromenes and spirochromenes were fabricated in a one-pot three-component synthesis manner from commercially available chemicals including phloroglucinol, malononitrile, and aldehydes/ isatines with acceptable and easy efficiencies. This methodology was performed in the presence of 2-hydroxyethylammonium formate as an effective and reusable ionic liquid catalyst. Water was selected as the reaction medium and the reaction was carried out at ambient temperature to create an environmentally friendly route. Other salient features of this method include catalyst chemical stability, good yields, short reaction times, and a simple work-up procedure.

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Design, synthesis and evaluation of dihydropyranoindole derivatives as potential cholinesterase inhibitors against Alzheimer’s disease

Cited by 18 publications

References 40 publications

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Facile one‐pot three‐component route to an assembly of 2‐amino‐4H‐chromenes and spirochromenes promoted via ceria nanoparticles in a benign manner

Synthesis of 2‐amino‐4H‐chromenes and spirochromenes using basic ionic liquid, 2‐hydroxyethylammonium formate as green, stable, and reusable catalyst

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