170872-48-7Relevant articles and documents
Synthesis of racemic 5-substituted 1-(2,3-dihydroxypropyl)-6-azauracils and their isosteric isomers
Tzeng,Hwang,Chen,Wei
, p. 1425 - 1435 (2007/10/03)
Acyclic nucleoside analogues of antiviral DHPA and HPMPA have been prepared. Coupling of silylated 6-azauracils with benzyl glycidyl ether and stannic chloride followed by the deprotection with boron trichloride gave 1- (2,3-dihydroxypropyl)-6-azauracils (3) in good overall yields. Reaction of silylated 6-azauracil and epichlorohydrin with or without catalytic stannic chloride afforded 1-(2-chloro-3-hydroxypmpyl)-6-azauracil (4a) and 1-(3- chloro-2-hydroxypropyl)-6-azauracil (6a) respectively. Coupling of silylated 6-azaisocytosine under the same reaction 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 herpes simplex viruses.