Abstract
Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl alpha-C-glycoside derivatives. The absolute configuration of 3-acetyl-2-methyl-5-(2'-chloro-D-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenocarcinoma / pathology*
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / pharmacology*
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Cell Line, Tumor / drug effects
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Chlorides / chemistry
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Fucose / analogs & derivatives*
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Fucose / chemistry
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Furans / chemistry*
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Glycosides / chemical synthesis
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Glycosides / pharmacology*
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Humans
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Lung Neoplasms / pathology*
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Magnetic Resonance Spectroscopy
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Structure-Activity Relationship
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Zinc Compounds / chemistry
Substances
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4-chloro-4-deoxygalactose
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Antineoplastic Agents
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Chlorides
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Furans
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Glycosides
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Zinc Compounds
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Fucose
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zinc chloride