3'hydroxyesorubicin halogenated at C-2'

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

New 3'-deamino-3'-hydroxy-2'-iodoesorubicin analogues were synthesized using optically active 4,6-dideoxyhex-1-enitol (7) as starting material. Direct coupling of daunomycinone (8) and 14-O-tert-butyldimethylsilyladriamycinone (9) with glycal 7 in the presence of N-iodosuccinimide gave 2'-iodo analogues 10 and 12. Deprotection of compounds 10 and 12 led to compounds 11 and 14, the 2'-iodinated, fully unblocked 4'-deoxy-3'-hydroxy congeners of daunorubicin (2) and doxorubicin (1). 2'-Iodo-3'-hydroxyesorubicin (14) showed cytotoxic activity similar to that of doxorubicin in vitro and higher antitumor activity against L-1210 leukemia than doxorubicin in vivo.

Original languageEnglish (US)
Pages (from-to)386-393
Number of pages8
JournalJournal of Antibiotics
Volume45
Issue number3
StatePublished - 1992
Externally publishedYes

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Doxorubicin
Leukemia L1210
Daunorubicin
3'-hydroxyesorubicin
daunomycinone
In Vitro Techniques
N-iodosuccinimide

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology

Cite this

3'hydroxyesorubicin halogenated at C-2'. / Priebe, W.; Neamati, N.; Perez-Soler, Roman.

In: Journal of Antibiotics, Vol. 45, No. 3, 1992, p. 386-393.

Research output: Contribution to journalArticle

Priebe, W, Neamati, N & Perez-Soler, R 1992, '3'hydroxyesorubicin halogenated at C-2'', Journal of Antibiotics, vol. 45, no. 3, pp. 386-393.
Priebe, W. ; Neamati, N. ; Perez-Soler, Roman. / 3'hydroxyesorubicin halogenated at C-2'. In: Journal of Antibiotics. 1992 ; Vol. 45, No. 3. pp. 386-393.
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