Zhijian Zhu, B. Lippa, L. Townsend
May 12, 1999
Citations
0
Influential Citations
5
Citations
Journal
Journal of Organic Chemistry
Abstract
The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(β-d-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(β-d-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(β-d-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. ...