3′-hydroxyesorubicin. Synthesis and antitumor activity

Waldemar Priebe, Nouri Neamati, Roman Perez-soler

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

A novel route to 4′-deoxy anthracycline analogues has been developed starting from previously unavailable, optically active 4, 6-dideoxy-hex-1-enitol 9. Coupling of daunomycinone (11) or 14-O-tert-butyldimethylsilyladriamycinone (12) with glycosyl chloride 10 in Koenigs-Knorr condition gave mainly a anomers, which were successfully deblocked to final 3′-deamino-4′-deoxy-3′-hydroxydaunorubicin (7) and 3′-deamino-3′-hydroxyesorubicin (8). Analogues were evaluated in vitro against P388 and L1210 leukemia and M5076 cells and in vivo against P388 leukemia. Compared with doxorubicin (1), 3′-hydroxyesorubicin (8) showed in vitro similar cytotoxic potential and in vivo higher antitumor activity.

Original languageEnglish (US)
Pages (from-to)838-846
Number of pages9
JournalThe Journal of Antibiotics
Volume43
Issue number7
DOIs
StatePublished - Jan 1 1990
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Fingerprint Dive into the research topics of '3′-hydroxyesorubicin. Synthesis and antitumor activity'. Together they form a unique fingerprint.

Cite this