o-Methylation on anthracyclines and anthracyclinones. New o-methyl ethers of daunorubicin and its analogues.

Abstract

The synthesis of four new ethers of daunorubicin, namely 6-, 9-, 11-monomethyl and 6,9-dimethyl, along with the 4'-methyl ethers of 11-deoxydaunorubicin and 11-deoxydoxorubicin is reported. While the methylation of any of the mentioned hydroxyl groups of the aglycone moiety of daunorubicin resulted in a practically complete loss of bioactivity, the methylation of the aminosugar hydroxyl group of 11-deoxydaunorubicin and 11-deoxydoxorubicin increased their effectiveness on P 388 leukemia in mice.

• Authors: G Cassinelli, F Di Matteo, S Forenza, M C Ripamonti, D Ruggieri, A Vigevani, F Arcamone
• Journal: Il Farmaco; edizione scientifica (Farmaco Sci) Vol. 37 Issue 8 Pg. 501-13 (Aug 1982) ISSN: 0430-0920 [Print] Italy
• PMID: 6957317 (Publication Type: Journal Article)

Chemical References

• Antibiotics, Antineoplastic
• Naphthacenes
• Daunorubicin

Topics

• Animals
• Antibiotics, Antineoplastic
• Daunorubicin (analogs & derivatives, chemical synthesis, pharmacology, therapeutic use)
• Drug Evaluation, Preclinical
• Leukemia P388 (drug therapy)
• Methylation
• Mice
• Naphthacenes (chemical synthesis, pharmacology, therapeutic use)