194228-60-9Relevant academic research and scientific papers
Synthesis and antiviral activity of novel erythrofuranosyl imidazo[1,2-α]pyridine C-nucleosides constructed via palladium coupling of iodoimidazo[1,2-α]pyridines and dihydrofuran
Gudmundsson, Kristjan S.,Williams, John D.,Drach, John C.,Townsend, Leroy B.
, p. 1449 - 1455 (2003)
2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) and certain analogues have shown significant activity against human cytomegalovirus. The metabolic instability of the glycosidic linkage in TCRB prompted us to synthesize the structurally similar imidazo[1,2-α]pyridine erythrofuranosyl C-nucleosides. As an approach to the synthesis of polychlorinated imidazo-[1,2-α]pyridine C-3-erythrofuranosides, a palladium-based methodology for coupling 2,3-dihydrofuran with chlorinated 3-iodoimidazo[1,2-α]pyridines was developed and optimized to give 80-90% yields of 2,6-dichloro- and 2,6,7-trichloro-3-(2,3-dideoxy-2,3-didehydro-D/L-erythrofuranosyl)- imidazo[1,2-α]pyridine. Dihydroxylation of these didehydro derivatives with osmium tetroxide or with AD-mix α gave a mixture of erythrofuranosyl C-nucleosides that were separated by standard and then chiral chromatography. When screened for anti-HCMV and HSV-1 activity, the α-D anomer of 2,6,7-trichloro-3-(erythrofuranosyl)imidazo[1,2-a]pyridine proved to be the most active member of the series, while the α-anomers all proved to be inactive.
Imidazo[1,2-a]pyridine C-nucleosides as antiviral agents
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, (2008/06/13)
This invention pertains to nucleoside analogs that have antiviral activity and improved metabolic stability, compositions comprising them, and methods of antiviral treatment employing them. More particularly, this invention pertains to imidazo[1,2-a]pyridine C-nucleosides, as exemplified by compounds such as imidazo[l,2-a]pyridine C5-nucleosides and imidazo[1,2-a]pyridine C3-nucleosides, and may be represented by formula (I), wherein exactly one of Q3and Q5is a sugar-like moiety; exactly one of Q3and Q5is —H; and Q2, Q6, Q7and Q8are independently imidazo[1,2-a]pyridine substituents, such as —H, —F, —Cl, —Br and —I.
