Syntheses of Isoxazoline-Carbocyclic Nucleosides and Their Antiviral Evaluation: A Standard Protocol

Quadrelli, Paolo; Martinez, Naiara Vazquez; Scrocchi, Roberto; Corsaro, Antonino; Pistarà, Venerando

doi:10.1155/2014/492178

Cited by 7 publications

(5 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The benzhydroxymoyl chloride 283 was treated with triethylamine and NMO in the presence of freshly distilled cyclopentadiene to afford the HDA cycloadduct 56 in 68% yield (Scheme ). the same procedure was followed for large-scale preparation of the HDA cycloadduct which served for the synthetic elaboration into several structures, including carbocyclic nucleosides and biomimetic compounds. − …”

Section: Nitrosocarbonyl Generation Methodsmentioning

confidence: 88%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

The nitrosocarbonyls (R-CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

show abstract

Section: Nitrosocarbonyl Generation Methodsmentioning

confidence: 88%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The modest antiviral activity showed by these compounds could be likely linked to the lack of substrate activity for cellular and/or viral nucleoside kinases, or alternatively, the lack of recognition of the compounds by the viral DNA or RNA polymerases. 59 The same strategy described above was applied for the synthesis of isoxazolino-carbocyclic nornucleosides incorporating an anthracene moiety through nitrosocarbonyl intermediates chemistry. A variety of analogues were attained starting from the already reported stereodefined heterocyclic aminols through the linear construction of purine heterocyclic rings.…”

Section: Scheme 19 Synthetic Strategy To Isoxazoline 52mentioning

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

View full text Add to dashboard Cite

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.

show abstract

“…99 The same strategy was applied for the synthesis of isoxazolinocarbocyclic nor-nucleosides incorporating an anthracene moiety through nitrosocarbonyl intermediates chemistry. The synthesis of the purine-nucleosides requires the two steps.…”

Section: Dielsàalder and Hetero Dielsàalder Reactions And The Antiviralsmentioning

confidence: 99%