Design, synthesis and evaluation of new chromone-derived aminophosphonates as potential acetylcholinesterase inhibitor

Shaikh, Sarfaraz; Dhavan, Pratik P.; Ramana, M. M. V.; Jadhav, B. L.

doi:10.1007/s11030-020-10060-y

Cited by 29 publications

(22 citation statements)

References 42 publications

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“…Interestingly, the new ortho -substituted aminophosphonate 8a was found to be the most active of all tested compounds with an IC 50 value of 1.215 µM towards AChE. This result corroborates with our theoretical prediction, presented later, and is in good agreement with some recently reported activities of different aminophosphonates on the cholinergic system [ 43 , 44 , 45 ]. For example, a chromone-derived aminophosphonate acts as an acetylcholinesterase inhibitor with IC 50 = 0.103 µM.…”

Section: Resultssupporting

confidence: 92%

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Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Kosińska

Virieux

Pirat

et al. 2022

IJMS

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The quest to find new inhibitors of biologically relevant targets is considered an important strategy to introduce new drug candidates for the treatment of neurodegenerative diseases. A series of (aminomethyl)benzylphosphonates 8a–c and their metallocarbonyl iron 9a–c and ruthenium 10a–c complexes were designed, synthesized, and evaluated for their inhibitory potentials against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) by determination of IC50. Metallocarbonyl derivatives, in general, did not show significant inhibition activity against these enzymes, the most potent inhibitor was the (aminomethyl)benzylphosphonate 8a (IC50 = 1.215 µM against AChE). Molecular docking analysis of AChE and (aminomethyl)benzylphosphonates 8a–c showed the strongest interactions of 8a and AChE compared to isomers 8b and 8c. Cytotoxicity studies of synthesized compounds towards the V79 cell line were also performed and discussed.

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Section: Resultssupporting

confidence: 92%

“…The docking studies of N -substituted α-aminophosphonate bearing a chromone moiety reveal that it binds to the peripheral anionic site and catalytic anionic site of AChE. The protonated amino group present in this compound is responsible for a cation–π interaction with TYR334 and H-bonding interaction with ASP72 [ 43 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Kosińska

Virieux

Pirat

et al. 2022

IJMS

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“…Further, a study by Shaikh et al 102 was related to the development of new chromone-derived aminophosphonates as a cholinesterase inhibitor using porcine pancreatic lipase (PPL) as a catalyst for the treatment of neurodegenerative diseases, as shown in Scheme 19. The authors found compound 38 as the most potent compound of the study with an IC 50 value of 0.1 μM for AChE.…”

Section: Chromones With Anti-neurodegenerative Propertiesmentioning

confidence: 99%

Recent advancements in chromone as a privileged scaffold towards the development of small molecules for neurodegenerative therapeutics

et al. 2022

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“…In a recent article, Shaikh et al . [ 265 ] designed a series of chromone-derived aminophosphonates in a one-pot reaction, catalyzed by porcine pancreatic lipase under solvent-free conditions. The α-aminophosphonates are a class of compounds with promising biological and pharmacologicalimportance as anti-AD agents [ 266 ].…”

Section: Chromone Derivativesmentioning

confidence: 99%

From Hybrids to New Scaffolds: The Latest Medicinal Chemistry Goals in Multi-target Directed Ligands for Alzheimer’s Disease

Alarcón-Espósito

Mallea

Rodríguez-Lavado

2021

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: Alzheimer’s disease (AD) is a chronic, progressive, and fatal neurodegenerative disorder affecting cognition, behavior, and function, being one of the most common causes of mental deterioration in elderly people. Once thought as being just developed because of β amyloid depositions or neurofibrillary Tau tangles, during the last decades, numerous ADrelated targets have been established, the multifactorial nature of AD became evident. In this context, the one drug-one target paradigm has resulted to be inefficient in facing AD and other disorders with complex etiology, opening the field for the emergence of the multitarget approach. In this review, we highlight the recent advances within this area, emphasizing in hybridization tools of well-known chemical scaffolds endowed with pharmacological properties concerning AD, such as curcumin-, resveratrol-, chromone- and indole-. We focus mainly on well stablished and incipient AD therapeutic targets, AChE, BuChE, MAOs, β-amyloid deposition, 5-HT4 and Serotonin transporter, with the aim to shed light about new insights in the AD multitarget therapy.

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Design, synthesis and evaluation of new chromone-derived aminophosphonates as potential acetylcholinesterase inhibitor

Cited by 29 publications

References 42 publications

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

Recent advancements in chromone as a privileged scaffold towards the development of small molecules for neurodegenerative therapeutics

From Hybrids to New Scaffolds: The Latest Medicinal Chemistry Goals in Multi-target Directed Ligands for Alzheimer’s Disease

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