Synthesis of racemic 5-substituted 1-(2,3-dihydroxypropyl)-6-azauracils and their isosteric isomers

Article abstract of DOI:10.1080/15257779508010702

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.

Full text of DOI:10.1080/15257779508010702

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Synthesis of Racemic 5-Substituted
1-(2,3-Dihydroxypropyl)-6-azauracils
and Their Isosteric Isomers
Cherng-Chyi Tzeng a , Long-Chih Hwang a , Chien-Chi Chen b &
Dau-Chang Wei c
a School of Chemistry, Kaohsiung Medical College , Kaohsiung
City, 807, Taiwan, Republic of China
b Culture Collection and Research Center , Food Industry
Research and Development Institute , Hsinchu, Taiwan
c Department of Pharmacy , Tajen Junior College of Pharmacy ,
Pingtung, Taiwan
Published online: 24 Sep 2006.
To cite this article: Cherng-Chyi Tzeng , Long-Chih Hwang , Chien-Chi Chen & Dau-Chang Wei
(1995) Synthesis of Racemic 5-Substituted 1-(2,3-Dihydroxypropyl)-6-azauracils and Their Isosteric
Isomers, Nucleosides and Nucleotides, 14:6, 1425-1435, DOI: 10.1080/15257779508010702
To link to this article: http://dx.doi.org/10.1080/15257779508010702
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