Formation of squaric acid amides of anthracycline antibiotics. Synthesis and cytotoxic properties

  • Bioorg Med Chem Lett. 2004 Sep 20;14(18):4783-9. doi: 10.1016/j.bmcl.2004.06.072.
Anna Tevyashova  1 ,  Ferenc Sztaricskai ,  Gyula Batta ,  Pál Herczegh ,  András Jeney
Affiliations
  • 1. 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.
PMID: 15324908 DOI: 10.1016/j.bmcl.2004.06.072
Abstract

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.