Nucleosides and Nucleotides p. 87 - 95 (1997)
Update date:2022-08-04
Topics:
Olsufyeva, Eugenia N.
Brusentsov, Nikolai A.
Todorova, Nedyalka
Balzarini, Jan
De Clercq, Erik
Preobrazhenskaya, Maria N.
Nucleoside dialdehydes were obtained by periodate oxidation of adenosine, cytidine, guanosine, uridine or 6-azauridine in the presence of Dowex (1x8; CH3COO-). Reductive alkylation of daunorubicin with these dialdehydes in the presence of NaBH3CN produced a series of 3'-deamino-3'- (4-morpholino)daunorubicin or 13-(R,S)-dihydrodaunorubicin derivatives, the latter being mixtures of two diastereomers at 13-C atom. The morpholino- daunorubicin derivatives containing nucleic base moieties are less cytotoxic than cyanomorpholino-daunorubicin, morpholino-daunorubicin and even than the parent antibiotic.
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