Cc. Tzeng et al., SYNTHESIS OF RACEMIC 5-SUBSTITUTED 1-(2,3-DIHYDROXYPROPYL)-6-AZAURACILS AND THEIR ISOSTERIC ISOMERS, Nucleosides & nucleotides, 14(6), 1995, pp. 1425-1435
Acyclic nucleoside analogues of antiviral DHPA and HPMPA have been pre
pared. Coupling of silylated 6-azauracils with benzyl glycidyl. ether
and stannic chloride followed by the deprotection with boron trichlori
de gave 1-(2,3-dihydroxypropyl)-6-azauracils (3) in good overall yield
s. Reaction of silylated 6-azauracil and epichlorohydrin with or witho
ut catalytic stannic chloride afforded 1-(2-chloro-3-hydroxypropyl)-6-
azauracil (4a) and 1-(3-chloro-2-hydroxypropyl)-6-azauracil (6a) respe
ctively. Coupling of silylated 6-azaisocytosine under the same reactio
n conditions provided 1-(2,3-dihydroxypropyl)-6-azaisocytosine (9) and
1-(2-chloro-3-hydroxypropyl)-6-azaisocytosine (10) respectively. None
of the compounds exhibited significant antiviral activity against her
pes simplex viruses.