Model studies towards the synthesis of 4'-azaerythrofuranosyladenines as analogues of the antiviral drug 2',3'-dideoxyadenosine (ddA)

被引：28

作者：

Leggio, A ^{[1
]}

Liguori, A ^{[1
]}

Maiuolo, L ^{[1
]}

Napoli, A ^{[1
]}

Procopio, A ^{[1
]}

Siciliano, C ^{[1
]}

Sindona, G ^{[1
]}

机构：

[1] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87030 ARCAVACATA,CS,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 20期

关键词：

D O I：

10.1039/a701279i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3097 / 3099

页数：3

共 22 条

[1]

BERRANGER T, 1995, TETRAHEDRON LETT, V36, P5523

[2] RELATIVE REACTIVITIES OF NORMAL AND ANGLE STRAINED CYCLO-OLEFINS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS - ROTATIONAL BARRIERS IN NITRONES [J].