91296-09-2Relevant academic research and scientific papers
Synthesis and Antiviral Activity of Carbocyclic Analogues of 2'-Deoxyribofuranosides of 2-Amino-6-substituted-purines and of 2-Amino-6-substituted-8-azapurines
Shealy, Y. Fulmer,O'Dell, C. Allen,Shannon, W. M.,Arnett, Gussie
, p. 1416 - 1421 (1984)
(+/-)-(1α,2β,4α)-4--2-hydroxycyclopentanemethanol (9) was synthesized by beginning with 2-amino-4,6-dichloropyrimidine and (+/-)-(1α,2β,4α)-4-amino-2-hydroxycyclopentanemethanol, preparing the 5- derivative of the resulting pyrimidine, and reducing the azo derivative.The carbocyclic analogue of 2-amino-6-chloropurine 2'-deoxyribofuranoside (10) was prepared from 9 and triethyl orthoformate, and the analogous 8-azapurine (11) was obtained by diazotizing 9.From 10 or 11, the carbocyclic analogues of 2'-deoxyguanosine, 2'-deoxythioguanosine, 2,6-diaminopurine 2'-deoxyribofuranoside, 2'-deoxy-8-azaguanosine, and 2,6-diamino-8-azapurine 2'-deoxyribofuranoside were prepared.All of these 2'-deoxyribofuranoside analogues were active against herpes simplex virus (types 1 and 2) replicating in cells in culture; some demonstrated potent activity.
