5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

Giofrè, Salvatore V.; Romeo, Roberto; Garozzo, A; Cicero, Nicola; Campisi, A.; Lanza, Giuseppe; Chiacchio, Maria Assunta

doi:10.3998/ark.5550190.p009.353

Cited by 5 publications

(2 citation statements)

References 29 publications

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“…The phosphonated derivatives had to be activated by intracellular phosphorylases and are also more resistant to enzymatic degradation because of the insensitive P−C bond. Their synthesis and biological evaluations were reviewed by Giofre et al 265 Homonucleosides, having a methyl group between the ring and the nucleobase, were also designed with the same goal. C-Nucleosides are physiologically present (i.e., pseudo uridine, for example).…”

Section: Natural Building Block Mimeticsmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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The isoxazolidine ring represents one of the privileged structures in medicinal chemistry, and there have been an increasing number of studies on isoxazolidine and isoxazolidine-containing compounds. Optimization of the 1,3-dipolar cycloaddition (1,3-DC), original methods including electrophilic or palladium-mediated cyclization of unsaturated hydroxylamine, has been developed to obtain isoxazolidines. Novel reactions involving the isoxazolidine ring have been highlighted to accomplish total synthesis or to obtain bioactive compounds, one of the most significant examples being probably the thermic ring contraction applied to the total synthesis of (±)-Gelsemoxonine. The unique isoxazolidine scaffold also exhibits an impressive potential as a mimic of nucleosides, carbohydrates, PNA, amino acids, and steroid analogs. This review aims to be a comprehensive and general summary of the different isoxazolidine syntheses, their use as starting building blocks for the preparation of natural compounds, and their main biological activities.

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Section: Natural Building Block Mimeticsmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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“…Higher SI values with respect to AZT indicated that the compounds were endowed with low cytotoxicity. 28 All these research activities were furtherly developed 29 and summarized by the Catania and Messina research groups in a Mini-Review dealing with phosphonated N,O-nuclesides 30 and in a review on the use of isoxazolidines as scaffolds for the preparation of biologically active compounds. 31 A general overview of the use of phosphonated nitrones for the synthesis of nucleoside analogues is given by Kokosza, Balzarini, and Piotrowska in a paper published on Nucleosides, Nucleotides and Nucleic Acids in 2014.…”

Section: Scheme 5 Synthesis Of Phosphonated No-nucleosides 15mentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Quadrelli¹,

Mella²,

Faita³

2023

Arkivoc

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Prominent in the current stage of drug development, antiviral compounds can be efficiently prepared through cycloaddition reactions. This review reports the use of 1,3-dipolar cycloadditions of nitrones, nitrile oxides and imines and other 1,3-dipoles in the light of their application for the preparation of synthons in the design and synthesis of compounds that were tested for their antiviral activities against a variety of viruses. Since nitrile oxides represent valuable precursors of nitrosocarbonyl intermediates, their use in the synthesis of antiviral compounds is reported. The products obtained from these pericyclic reaction approaches were tested for their activities in terms of blocking the virus replication and the relevant biological data are highlighted.

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Synthesis of 1,2,3‐Triazoles Bearing a 4‐Hydroxyisoxazolidine Moiety from 4,5‐Unsubstituted 2,3‐Dihydroisoxazoles

et al. 2020

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A synthetic approach towards new 1,2,3‐triazoles bearing the 3‐hydroxymethylated 4‐hydroxyisoxazolidine moiety has been described. The strategy has relied on dihydroxylation and epoxidation reactions of 4,5‐unsubstituted 2,3‐dihydroisoxazoles, allowing the introduction of the hydroxy group at the isoxazolidine ring in a trans stereoselective manner with respect to the substituent at C‐3 carbon atom. The requisite 5‐azidoisoxazolidines have been prepared from activated isoxazolidines possessing a good leaving group at C‐5 carbon atom by treatment with trimethylsilyl azide and Lewis acid (isoxazolidinyl benzoates) or with sodium azide (chloroisoxazolidines). The 1,2,3‐triazole moiety has been synthesized through copper(I)‐catalyzed azide‐alkyne cycloaddition.

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5-(3-Phosphonated 1H-1,2,3-triazol-4-yl)isoxazolidines: synthesis, DFT studies and biological properties

Cited by 5 publications

References 29 publications

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Synthesis of 1,2,3‐Triazoles Bearing a 4‐Hydroxyisoxazolidine Moiety from 4,5‐Unsubstituted 2,3‐Dihydroisoxazoles

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