In silico molecular docking and in vitro antioxidant activity studies of novel α-aminophosphonates bearing 6-amino-1,3-dimethyl uracil

Nayab, Rasool Shaik; Maddila, Suresh; Krishna, Murthy Potla; Titinchi, Salam J.J.; Thaslim, Basha Shaik; Venkataramaiah, Chintha; Rajendra, Wudayagiri; Venkateswarlu, N. B.; Vijaya, Tartte; Chinnam, Sampath; Chamarthi, Naga Raju

doi:10.1080/10799893.2020.1722166

Cited by 44 publications

(36 citation statements)

References 38 publications

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“…The phosphonic α-amino acids and their derivatives has a considerable role play in the design of new drugs [1]. Thus, these derivatives have a high potential for diverse biological activity [2], acting as a protease inhibitor agent of West Nile virus [3], anticancer agent [4], antibacterial [5], antioxidant [6]. Their various applications are also oriented in the inhibitory use of bone resorption [7], [8].…”

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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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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“…Impetus, by the findings and less explored scaffold of 1,3‐dimethyl‐6‐amino‐5‐nitoso uracil and amides, herein, we successfully report a novel strategy for the synthesis of uracil‐based amide derivatives. The results obtained bypass the typical challenges in the synthesis of amides Over a decade, uracil and its derivatives have shown to exhibit antiviral and anticancer properties, which were proven both computationally as well as experimentally [21–24] . While newly discovered, 6‐amino‐1,3‐dimethyl uracil was shown to be used as an antioxidant agent [25] .…”

Section: Introductionmentioning

confidence: 86%

“…The results obtained bypass the typical challenges in the synthesis of amides Over a decade, uracil and its derivatives have shown to exhibit antiviral and anticancer properties, which were proven both computationally as well as experimentally. [21][22][23][24] While newly discovered, 6amino-1,3-dimethyl uracil was shown to be used as an antioxidant agent. [25] Majority of uracil derivatives are used as inhibitors of acetylcholinesterase (AchE) and butyrlcholinesterase (BuCHe), the key molecules involved in Alzheimer's disease.…”

Section: Introductionmentioning

confidence: 99%

Direct Synthesis, Characterization and Theoretical Studies of N‐(6‐Amino‐1,3‐dimethyl‐2,4‐dioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐yl)benzamide Derivatives

et al. 2021

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With the far-flung importance of uracil and amides in innumerable fields of chemistry and biology, a coherent synthesis that nullifies the use of prodigal reagents, methods and catalysts are hugely accepted. From the present outcomes, we report a highly atom profitable nucleophilic addition reaction of aromatic aldehydes and heterocyclic amines for the generation of amides having an excellent yield and high reproducibility. The main force responsible for the forward reaction is the presence of the nitroso group at the C-5 position on uracil scaffold, which drives the formation of formidable range products. The conclusive mechanism is based on the dehydrogenation reaction of the carbinolamine product formed during the nucleophilic addition reaction of the aromatic aldehyde with the free heterocyclic amino group to yield the corresponding amides. The synthesized compounds were predicated for biological properties and proved it to be an ideal G protein-coupled receptor kinase2 (GRK2) inhibitor. Out of all, the compound 3 f showed the most preeminent properties when compared to Paroxetine, studied using molecular docking. At the same time, computed ADME analysis proved them as an ideal drug candidate. Our findings not only prophesize new methods for the synthesis of bioactive-amides using a cross-coupling strategy but also demonstrates their novel applications as a human GRK2 inhibitor.

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“…6-Amino-1,3-dimethyluracil ( 38 ) was found to be a good starting material in condensation with benzaldehyde derivatives and diethyl phosphite. Phosphorus pentoxide in methanesulfonic acid (1:10), known as Eaton’s reagent, was the catalyst ( Scheme 31 ) [ 54 ].…”

Section: Kabachnik–fields Reactions With Dialkyl Phosphites Alkyl H -Phosphinates and Secondary Phosphine Oxidesmentioning

confidence: 99%

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Varga

Keglevich

2021

Molecules

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The Kabachnik–Fields reaction, comprising the condensation of an amine, oxo compound and a P-reagent (generally a >P(O)H species or trialkyl phosphite), still attracts interest due to the challenging synthetic procedures and the potential biological activity of the resulting α-aminophosphonic derivatives. Following the success of the first part (Molecules 2012, 17, 12821), here we summarize the synthetic developments in this field accumulated in the last decade. The procedures compiled include catalytic accomplishments as well as catalyst-free and/or solvent-free “greener” protocols. The products embrace α-aminophosphonates, α-aminophosphinates, and α-aminophosphine oxides along with different bis derivatives from the double phospha-Mannich approach. The newer developments of the aza-Pudovik reactions are also included.

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In silico molecular docking and in vitro antioxidant activity studies of novel α-aminophosphonates bearing 6-amino-1,3-dimethyl uracil

Cited by 44 publications

References 38 publications

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

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

Direct Synthesis, Characterization and Theoretical Studies of N‐(6‐Amino‐1,3‐dimethyl‐2,4‐dioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐yl)benzamide Derivatives

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

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