Synthesis and antiviral activity of anthracene derivatives of isoxazolino-carbocyclic nucleoside analogues

Memeo, Misal Giuseppe; Lapolla, Francesco; Maga, Giovanni; Quadrelli, Paolo

doi:10.1016/j.tetlet.2015.02.114

Cited by 14 publications

(13 citation statements)

References 61 publications

(10 reference statements)

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“…Hence, the two stalks could be used as healthy foods due to the high nutritional values and phenolic acids. In addition, flavones have a significant positive effect on diseases related to oxidative stress and inflammatory by regulating multiple cell signaling pathways and alterations in multiple cellular signaling pathways, such as NF-κB signaling pathway ( 49 ), and anthracene derivatives have the cytotoxicity and antiviral properties ( 50 ). Hence, SRT has better antioxidant and antiinflammatory activities than SRO.…”

Section: Resultsmentioning

confidence: 99%

High Value-Added Application of Two Renewable Sources as Healthy Food: The Nutritional Properties, Chemical Compositions, Antioxidant, and Antiinflammatory Activities of the Stalks of Rheum officinale Baill. and Rheum tanguticum Maxim. ex Regel

et al. 2022

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Rhubarb plants (Rheum officinale and R. tanguticum) have edible stalks. In this work, we aimed to compare the nutritional properties, chemical compositions, and bioactivities of R. officinale (SRO) and R. tanguticum (SRT) stalks and to analyze the composition–function relationship. Results showed that the two stalks were good sources of fiber, as well as minerals. They contained abundant essential amino acids and essential fatty acids to regulate the immunity and prevent some chronic diseases; the contents of polyunsaturated fatty acids were 2,244.32 mg/100 g and 2,844.69 mg/100 g, respectively. The antioxidant activity were also proved. Metabolomics showed that SRO and SRT contained abundant phenolic acids. Due to the higher concentrations of flavones, SRT has better antiinflammatory activities than SRO by inhibiting NF-κB signaling pathway. Rhubarb stalks exhibited good safety in acute toxicity and cytotoxicity tests. This work indicated that the two stalks have nutritional value, safety, and bioactivities, and could be used as sources of nutritional ingredients for regulating the immunity of body in food industry.

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Section: Resultsmentioning

confidence: 99%

High Value-Added Application of Two Renewable Sources as Healthy Food: The Nutritional Properties, Chemical Compositions, Antioxidant, and Antiinflammatory Activities of the Stalks of Rheum officinale Baill. and Rheum tanguticum Maxim. ex Regel

et al. 2022

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“…Previous results demonstrated that compound 4 b of Figure can be anchored at the receptor pocket involved in the protein‐protein interaction (PPI, point 4 of Figure ) through the isoxazoline ring and the histidine His32 residue. The anthracene and the uracil substituted cyclopentanol moieties are perfectly complementary to the pocket involved in the PPI, and the anthracene substituent shades a hydrophobic pocket involved in the specific E2‐E1 interaction …”

Section: Resultsmentioning

confidence: 99%

Pericyclic Reactions for Anti‐HPV Antivirals: Unconventional Nucleoside Analogue Synthesis via Nitrosocarbonyl Chemistry

2017

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A new adenine derivative is prepared through the chemistry of nitrosocarbonyl intermediates. The synthesis relies upon the functionalization of adenine by inserting an ester moiety, to be transformed into the corresponding hydroxamic acid. The oxidation conducted in situ in the presence of cyclopentadiene afforded the hetero Diels‐Alder cycloadduct, furtherly elaborated to give the target nucleoside analogue. This single product displayed a selective high activity against HPV. The EC50 and EC90 values are remarkably lower than the values collected for Cidofovir used as control drug. The EC50 is 39 times lower while the CC50 value is 97.11 μM.

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“…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: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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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.

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Synthesis and antiviral activity of anthracene derivatives of isoxazolino-carbocyclic nucleoside analogues

Cited by 14 publications

References 61 publications

High Value-Added Application of Two Renewable Sources as Healthy Food: The Nutritional Properties, Chemical Compositions, Antioxidant, and Antiinflammatory Activities of the Stalks of Rheum officinale Baill. and Rheum tanguticum Maxim. ex Regel

High Value-Added Application of Two Renewable Sources as Healthy Food: The Nutritional Properties, Chemical Compositions, Antioxidant, and Antiinflammatory Activities of the Stalks of Rheum officinale Baill. and Rheum tanguticum Maxim. ex Regel

Pericyclic Reactions for Anti‐HPV Antivirals: Unconventional Nucleoside Analogue Synthesis via Nitrosocarbonyl Chemistry

Generation and Trapping of Nitrosocarbonyl Intermediates

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