title: A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety.
abstract: Treatment of the squaric acid amide esters (7, 9) of anthracycline glycoside antibiotics with aliphatic and aromatic primary and secondary amines, amino acids, peptides and aminodeoxy sugars furnished the new asymmetric diamides 16-19, 25-30, 32, 34 and 38-40 in stereoselective reactions which do not require protecting group-manipulations. The IC50 = 0.12 microM value measured for daunorubicin (1) on human leukemia (HL-60) cells is comparable to those obtained for the daunomycin-L-leucyl squaric acid diamide (30, IC50 = 0.18 microM) and the corresponding D-galactosamine derivative (40, IC50=0.22 microM).
authors.affiliation: Research Group for Antibiotics of the Hungarian Academy of Sciences, and Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, Hungary. sztarife@delfin.klte.hu
authors.forename: Ferenc
authors.initials: F
authors.lastname: Sztaricskai
authors.forename: Anita
authors.initials: A
authors.lastname: Sum
authors.forename: Erzsébet
authors.initials: E
authors.lastname: Roth
authors.forename: István F
authors.initials: IF
authors.lastname: Pelyvás
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Sándor
authors.forename: Gyula
authors.initials: G
authors.lastname: Batta
authors.forename: Pál
authors.initials: P
authors.lastname: Herczegh
authors.forename: Judit
authors.initials: J
authors.lastname: Reményi
authors.forename: Zsanett
authors.initials: Z
authors.lastname: Miklán
authors.forename: Ferenc
authors.initials: F
authors.lastname: Hudecz
mesh_terms: D018943:Anthracyclines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D003503:Cyclobutanes / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure
chemical_list: D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D003503:Cyclobutanes; C030042:squaric acid