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 μM 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 μM) and the corresponding D-galactosamine derivative (40, IC50 = 0.22 μM).
- Anthracycline glycoside antibiotics
- HL-60 activity
- Squaric acid amides
ASJC Scopus subject areas
- Drug Discovery