Design, synthesis and evaluation of pyrazole bearing α-aminophosphonate derivatives as potential acetylcholinesterase inhibitors against Alzheimer’s disease

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

doi:10.1016/j.bioorg.2020.103589

Cited by 59 publications

(19 citation statements)

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“…Recently, α-aminophosphonates have received enormous attention from scientific researchers in pharmaceutical and medicinal chemistry [ 30 ], due to structural analogies to amino acids and exhibit many biological properties [ 31 ], such as anti-Alzheimer [ 32 ], antimicrobial [ 33 ], antiviral [ 34 ], and antioxidant [ 35 ]. The Kabachnik–Fields reaction is one and the simplest of the most practical approaches for α-aminophosphonate syntheses; the reaction generally requires various catalysts, such as CF 3 CO 2 H [ 36 ], TiO 2 [ 37 ], Amberlite-IR 120 [ 38 ], SnCl 2 [ 39 ], phenyl phosphonic acid [ 40 ], and ethyl lactate [ 41 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

et al. 2021

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“…This wide range of therapeutic and pharmacological activity [9] has led researchers to promote new methods for the preparation of α-amino phosphonic acid [10], whose main routes are the one-pot reaction of Kabachnick field [11]- [13] and the synthesis of chiral products of α-amino phosphonates [14]- [16]. In this case, the synthesis of new heterocyclic phosphonic amino esters continues to bloom in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Khadir

Boukhssas

Achamlale³

et al. 2021

EJCHEM

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The biheterocyclic derivative of the phosphonic glycine analogue is prepared selectively by reaction between the α-azidoamino diethyl methylphosphonate and the 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole. The dipolar -1,3 cycloaddition reaction using Click Chemistry was carried out in a solvent water/ethanol mixture in a ratio of 1:1. Copper sulphate pentahydrate and sodium ascorbate are used in the reaction in catalytic amounts. The compound [diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}(benzamido) methyl] phosphonate was isolated pure as a white powder, after chromatography on a silica gel column (ethyl acetate/hexane acetate: 1/1). The yield of pure product is 90%, after recrystallization in an ether/hexane mixture. The structure of the -1,4 isomer is attributed to the compound obtained by means of 1D and 2D NMR and based on data from the literature concerning the cycloaddition reaction via Click Chemistry. Two-dimensional NMR spectroscopy played a major role. The analysis of the different correlations between adjacent hydrogens and carbons, and also between hydrogens and distant carbons, confirmed the proposed structure.

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“…For instance, the pyrazole analogs exhibit cytotoxicity against DLA cells, reduces tumour loads, and downregulates tumour progression proliferation [ 10 ]. The pyrazole derivatives have antidiabetic and anti-inflammatory [ 11 ], antimicrobial [ 12 ], and acetylcholinesterase inhibitor [ 13 ] properties. The Salvia officinalis L belongs to Lamiaceae family is known for its antioxidant and many pharmaceutical potencies, like anti-spasmodic, astringent, sedative, anti-hyperglycemic, and anti-inflammatory [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

Kumara

Prabhudeva

Vagish

et al. 2021

Heliyon

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In a sustained search for novel and effective antioxidants, a potential therapeutic leads against renal, and neurological disorders. Amongst the heterocycles, pyrazole and their derivatives have been extensively studied for their biological potencies, particularly to a larger extent for their antioxidant properties. Although many of pyrazole derivatives displayed antioxidant activities, still there is a need of developing efficient protocol for their synthesis, involving ecofriendly conditions, molecules of greater antioxidant efficacy and lesser toxicity, etc. In this context, the current study presents an amberlyst-15 catalysed efficient synthesis of 2-pyrazoline derivatives, 5 ( a - g ) via (3 + 2) annulation of chalcones with phenylhydrazines. Structure proofs of new pyrazoles offered by spectral studies, and the molecular structure of compound 5d of the series by crystallographic studies, which revealed an intra molecular hydrogen bond interactions (C–H⋯N type), and stabilization by C–H...π and π---π molecular interactions. Of the series, compounds 5g and 5h show excellent DPPH (IC 50 = 0.245 ± 0.01, and 0.284 ± 0.02 μM); and hydroxyl (IC 50 = 0.905 ± 0.01, and 0.892 ± 0.01μM) radical scavenging activities comparable with respective controls, ascorbic acid (IC 50 = 0.483 ± 0.01μM) and BHA (IC 50 = 1.739 ± 0.01μM). The molecular docking and ADME/Tox studies indicate that, these compounds have good antioxidant activity through π-π stacking with Catalase via Try337 and Phe140, and therefore, might be lead antioxidants for further study.

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Design, synthesis and evaluation of pyrazole bearing α-aminophosphonate derivatives as potential acetylcholinesterase inhibitors against Alzheimer’s disease

Cited by 59 publications

References 51 publications

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

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