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Syntheses of isoxazoline-carbocyclic nucleosides and their antiviral evaluation: a standard protocol.

Quadrelli P, Vazquez Martinez N, Scrocchi R, Corsaro A, Pistarà V - ScientificWorldJournal (2014)

Bottom Line: Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds.No specific antiviral activity was observed in the cases at hand.Novel compounds were prepared for future biological tests.

View Article: PubMed Central - PubMed

Affiliation: Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

ABSTRACT
The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.

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Related in: MedlinePlus

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Related In: Results  -  Collection


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Mentions: The synthetic route to uracil and thymine nucleosides involves the steps illustrated in Scheme 4 and started with the preliminary preparation of the isocyanates whose quality and purity strongly determine the yields of the final compounds. The condensations of the isocyanates with aminols 11a,b were performed at –20°C in anhydrous DMF solutions and the reactions left at room temperature for 12 h. The urea adducts 15a,b were obtained in 82% yields and found identical with authentic samples previously prepared [13]. Cyclization of the ureas 15a,b took place smoothly upon gentle refluxing in 2 M H2SO4 solution for 3 h. The uracil nucleosides 16Ua,b and the thymine analogues 16Ta,b were isolated from these solutions after pH adjustment to 7 and extraction with dichloromethane. The yields of the cyclization steps were satisfactorily improved (95%, +20%) and the structures confirmed through spectroscopic analyses.


Syntheses of isoxazoline-carbocyclic nucleosides and their antiviral evaluation: a standard protocol.

Quadrelli P, Vazquez Martinez N, Scrocchi R, Corsaro A, Pistarà V - ScientificWorldJournal (2014)

© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4230217&req=5

Mentions: The synthetic route to uracil and thymine nucleosides involves the steps illustrated in Scheme 4 and started with the preliminary preparation of the isocyanates whose quality and purity strongly determine the yields of the final compounds. The condensations of the isocyanates with aminols 11a,b were performed at –20°C in anhydrous DMF solutions and the reactions left at room temperature for 12 h. The urea adducts 15a,b were obtained in 82% yields and found identical with authentic samples previously prepared [13]. Cyclization of the ureas 15a,b took place smoothly upon gentle refluxing in 2 M H2SO4 solution for 3 h. The uracil nucleosides 16Ua,b and the thymine analogues 16Ta,b were isolated from these solutions after pH adjustment to 7 and extraction with dichloromethane. The yields of the cyclization steps were satisfactorily improved (95%, +20%) and the structures confirmed through spectroscopic analyses.

Bottom Line: Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds.No specific antiviral activity was observed in the cases at hand.Novel compounds were prepared for future biological tests.

View Article: PubMed Central - PubMed

Affiliation: Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

ABSTRACT
The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.

Show MeSH
Related in: MedlinePlus