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Synthesis and antitumor activity of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycinone derivatives modified at C-3' or C-4'.

Abstract
As a part of a study to exploit anthracycline glycosides effective against resistant tumor cells, the 3'-O-methyl (3), 4'-O-methyl (4), 3'-deoxy (6), 3'-deoxy-3'-fluoro (7), and 3'-deoxy-3'-iodo (8) derivatives of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)daunomycinone have been prepared by coupling suitably protected glycosyl bromides with daunomycinone. The doxorubicin-type analog (5) of 4 was also prepared. Among the compounds prepared, 5 showed the highest antitumor activity. Relationships between chemical structures of the synthetic products and antitumor activities, together with the degree of resistance were discussed.
AuthorsY Takagi, N Kobayashi, M S Chang, G J Lim, T Tsuchiya
JournalCarbohydrate research (Carbohydr Res) Vol. 307 Issue 3-4 Pg. 217-32 (Feb 1998) ISSN: 0008-6215 [Print] Netherlands
PMID9675364 (Publication Type: Comparative Study, Journal Article)
Chemical References
  • 7-O-(2,6-dideoxy-2-fluoro-4-O-methyltalopyranosyl)adriamycinone
  • Antibiotics, Antineoplastic
  • 7-O-(2,6-dideoxy-2-fluorotalopyranosyl)daunomycinone
  • Doxorubicin
  • Daunorubicin
Topics
  • Animals
  • Antibiotics, Antineoplastic (chemical synthesis, chemistry, pharmacology)
  • Cell Division (drug effects)
  • Daunorubicin (analogs & derivatives, chemistry, pharmacology)
  • Doxorubicin (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Leukemia L1210 (pathology)
  • Leukemia P388 (pathology)
  • Mice
  • Neoplasm Transplantation
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

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