Structure-activity relationships of elloramycin and tetracenomycin C.
The structure-activity relationships of the anthracycline-related antibiotics of the tetracenomycin C/elloramycin-type were investigated by derivatization of elloramycin (1) and elloramycinone (2). During hydrolysis experiments a unique transglycosylation reaction was discovered, converting elloramycin (1) into isoelloramycin (10) by treatment with anhydrous trifluoroacetic acid. Following the proposed structure-activity relationship concept, 8-O-methylelloramycinone (14) was synthesized from elloramycinone (2), and was shown to be the most active derivative according to the proliferation inhibition assay against murine L1210 leukemia cells.
Institut für Organische Chemie, Universität Göttingen, W. Germany.
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Rohr
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Zeeck
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D006031:Glycosylation; D006868:Hydrolysis; D007939:Leukemia L1210; D008745:Methylation; D051379:Mice; D009279:Naphthacenes / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D009279:Naphthacenes; C020938:tetracenomycin C; C047329:elloramycin