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.
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Authors | Y Takagi, N Kobayashi, M S Chang, G J Lim, T Tsuchiya |
Journal | Carbohydrate research
(Carbohydr Res)
Vol. 307
Issue 3-4
Pg. 217-32
(Feb 1998)
ISSN: 0008-6215 [Print] Netherlands |
PMID | 9675364
(Publication Type: Comparative Study, Journal Article)
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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
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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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