期刊
JOURNAL OF MEDICINAL CHEMISTRY
卷 46, 期 8, 页码 1449-1455出版社
AMER CHEMICAL SOC
DOI: 10.1021/jm020339r
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资金
- NIAID NIH HHS [5-P01-AI46390, U19-AI31718] Funding Source: Medline
- NIGMS NIH HHS [T32-GM07767] Funding Source: Medline
2,5,6-Trichloro-1-(beta-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-a]pyridine erythrofuranosyl C-nucleosides. As an approach to the synthesis of polychlorinated imidazo[1,2-alpyridine C-3-erythrofuranosides, a palladium-based methodology for coupling 2,3-dihydrofuran with chlorinated 3-iodoimidazo[1,2-a]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-a]pyridine. Dihydroxylation of these didehydro derivatives with osmium tetroxide or with AD-mix alpha 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 alpha-D anomer of 2,6,7-trichloro-3-(erythrofuranosyl)imidazo[1,2-alpyridine proved to be the most active member of the series, while the beta-anomers all proved to be inactive.
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