The [3 + 2] dipolar cycloaddition of nitrones to N-9-vinyladenine provides a regioselective and stereoselective method for the obtainment of 4'-aza-analogues of 2',3'-dideoxyadenosine. The latter may act as antiviral agents by analogy with the behaviour in vitro of the corresponding thymine analogue. The formation of the unsubstituted isoxazolidino derivative requires the protection of the 6-NH2 function of the dipolarophile, which is not necessary when preformed nitrones are used. The obtainment of a specific enantiomer has been exploited by enzyme-catalysed hydrolysis of an ester function introduced into the isoxazolidino nucleus.
The [3 + 2] dipolar cycloaddition of nitrones to N-9-vinyladenine provides a regioselective and stereoselective method for the obtainment of 4′-aza-analogues of 2′,3′-dideoxyadenosine. The latter may act as antiviral agents by analogy with the behaviour in vitro of the corresponding thymine analogue. The formation of the unsubstituted isoxazolidino derivative requires the protection of the 6-NH2 function of the dipolarophile, which is not necessary when preformed nitrones are used. The obtainment of a specific enantiomer has been exploited by enzyme-catalysed hydrolysis of an ester function introduced into the isoxazolidino nucleus.
Model studies towards the synthesis of 4'-azaerythrofuranosyl-adenines as analogues of the antiviral drug 2',3'-dideoxyadenosine (ddA)
LEGGIO, Antonella;Liguori A;MAIUOLO, Loredana;SICILIANO, Carlo;SINDONA, Giovanni
1997-01-01
Abstract
The [3 + 2] dipolar cycloaddition of nitrones to N-9-vinyladenine provides a regioselective and stereoselective method for the obtainment of 4′-aza-analogues of 2′,3′-dideoxyadenosine. The latter may act as antiviral agents by analogy with the behaviour in vitro of the corresponding thymine analogue. The formation of the unsubstituted isoxazolidino derivative requires the protection of the 6-NH2 function of the dipolarophile, which is not necessary when preformed nitrones are used. The obtainment of a specific enantiomer has been exploited by enzyme-catalysed hydrolysis of an ester function introduced into the isoxazolidino nucleus.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
