Efficient synthesis and antitumor activity of novel 14-fluoroanthracyclines

✍ Scribed by Teruyo Matsumoto; Masako Ohsaki; Fuyuhiko Matsuda; Shiro Terashima

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 263 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96527-4

✦ Synopsis

The title compounds, (+)-14-fluoro-4-demethoxy-and (+)-14-fluorodaunorubicin, were synthesized from (-)-7-deoxy-4-demethoxy-and (-)-7-deoxydaunomycinone, respectively, by featuring the novel fluorination reaction in which tetrabuthylammonium fluoride is employed in the presence of a half equiv of p-toluenesulfonic acid as a key step. These novel anthracyclines were found to exhibit significant inhibitory activity against P388 murine leukemia in vitro and in viva. The anthracyclines, adriamycin (1) and daunorubicin (Z), are of great current interest because of their activity againstmanytypes of human cancers. '*' However, their uses for cancer chemotherapy are seriously hampered by their side effects, especially by dose-related We are grateful to Dr.