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.
Rohr
J
J
Institut für Organische Chemie, Universität Göttingen, W. Germany.
Zeeck
A
A
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