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

Anna Tevyashova; Ferenc Sztaricskai; Gyula Batta; Pál Herczegh; András Jeney

doi:10.1016/j.bmcl.2004.06.072

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.

Authors

Anna Tevyashova¹, Ferenc Sztaricskai, Gyula Batta, Pál Herczegh, András Jeney

Affiliation

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.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Amides / pharmacology
Anthracyclines / chemical synthesis*
Anthracyclines / chemistry
Anthracyclines / pharmacology
Antibiotics, Antineoplastic / chemical synthesis*
Antibiotics, Antineoplastic / chemistry
Antibiotics, Antineoplastic / pharmacology
Cell Line, Tumor
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cyclobutanes / chemical synthesis*
Cyclobutanes / chemistry
Cyclobutanes / pharmacology
Drug Screening Assays, Antitumor
Humans
Mass Spectrometry
Structure-Activity Relationship

Substances

Amides
Anthracyclines
Antibiotics, Antineoplastic
Cyclobutanes
squaric acid