Highly functionalised potential neuraminidase (NA) inhibitors, analogues of peramivir, were synthesised via a new and versatile method starting from a stereoselective 1,3-dipolar cycloaddition reaction between the nitrile oxide derived from 2-ethylbutanal and the commercially available and inexpensive cyclopentadiene and 1,3-cyclohexadiene, which afforded the isoxazolino-cyclopentene or cyclohexene intermediates, respectively. The subsequent reaction of the C=C bond in different conditions allowed the functionalisation of the five (or six) membered carbon nucleus. Further functionalised derivatives displaying an amino and a hydroxyl group were achieved via the final opening of the isoxazoline ring.
New Strategy of Synthesis of Peramivir Analogues as Potential Neuraminidase Inhibitors / R. Bartolotta, C. La Rosa, D. Nava. - In: SYNTHESIS. - ISSN 0039-7881. - 52:6(2020 Mar 17), pp. 933-941.
Titolo: | New Strategy of Synthesis of Peramivir Analogues as Potential Neuraminidase Inhibitors |
Autori: | BARTOLOTTA, ROBERTA (Primo) NAVA, DONATELLA (Ultimo) |
Parole Chiave: | peramivir; neuraminidase inhibitors; 1,3-dipolar cycloaddition; isoxazolines; cyclopentadiene; 1,3-cyclohexadiene; |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 17-mar-2020 |
Rivista: | |
Tipologia: | Article (author) |
Data ahead of print / Data di stampa: | dic-2019 |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1055/s-0039-1690039 |
Appare nelle tipologie: | 01 - Articolo su periodico |
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