3'-Hydroxyesorubicin. Synthesis and antitumor activity

W. Priebe, N. Neamati, Roman Perez-Soler

Research output: Contribution to journalArticle

7 Citations (Scopus)

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 α 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 otential and in vivo higher antitumor activity.

Original languageEnglish (US)
Pages (from-to)838-846
Number of pages9
JournalJournal of Antibiotics
Volume43
Issue number7
StatePublished - 1990
Externally publishedYes

Fingerprint

Leukemia P388
Leukemia L1210
Anthracyclines
Doxorubicin
Chlorides
3'-hydroxyesorubicin
In Vitro Techniques
daunomycinone
3'-deamino-3'-hydroxydaunorubicin

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology

Cite this

3'-Hydroxyesorubicin. Synthesis and antitumor activity. / Priebe, W.; Neamati, N.; Perez-Soler, Roman.

In: Journal of Antibiotics, Vol. 43, No. 7, 1990, p. 838-846.

Research output: Contribution to journalArticle

Priebe, W, Neamati, N & Perez-Soler, R 1990, '3'-Hydroxyesorubicin. Synthesis and antitumor activity', Journal of Antibiotics, vol. 43, no. 7, pp. 838-846.
Priebe, W. ; Neamati, N. ; Perez-Soler, Roman. / 3'-Hydroxyesorubicin. Synthesis and antitumor activity. In: Journal of Antibiotics. 1990 ; Vol. 43, No. 7. pp. 838-846.
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