Formation of squaric acid amides of anthracycline antibiotics. Synthesis and cytotoxic properties.
The reaction of the anthracycline glycoside antibiotics 1-3 with the squaric acid ester 4 gave the squaric acid amide esters 5-7 under neutral conditions, whereas over pH7 the products are the symmetric diamides (8, 9, 11, and 12). Of the prepared compounds 11 was the most active on MCF-7 human mammary adenocarcinoma cells.
Research Group for Antibiotics of the Hungarian Academy of Sciences, and Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, PO Box 70, H-4010 Hungary.
Anna
A
Tevyashova
Ferenc
F
Sztaricskai
Gyula
G
Batta
Pál
P
Herczegh
András
A
Jeney
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018943:Anthracyclines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D013058:Mass Spectrometry; D013329:Structure-Activity Relationship
D000577:Amides; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D003503:Cyclobutanes; C030042:squaric acid