Fluorinated anthracyclines: synthesis and biological activity.
Organic structures with fluorine atom are slightly diffuse in nature. Starting  80s researchers have discovered that the selective introduction of fluorine into biologically active molecules exercised an influence on activity. So an important endeavour in drug design have been described and numerous compounds incorporating fluorine as either a bioisosteric replacement for hydrogen or an isoelectronic replacement for the hydroxyl group have been reported. Parallely, an enormous literature on anthracyclines exists, a class of compounds used in clinical since  70s, as antitumor drugs. Unfortunately, the anthracyclines are known as well for several toxical effects that frequently condition the clinical use. In the last decade a lot of anthracycline derivatives has been described in which has been introduced a fluorine atom in different position of molecule. This review wishes to represent an updated collection of compounds with anthracycline structure where a fluorine atom has been introduced on aglycon or/and sugar moiety. Together with the chemical structures, the synthetic indications are furnished and succinct explanations of biological activity are summarised (if available).
Giannini
Giuseppe
G
Dept. of Chemistry - Sigma-Tau, via Pontina Km 30, (Rome), 400 I-00040 Pomezia, Italy. giuseppe.giannini@sigma-tau.it
D000818:Animals; D018943:Anthracyclines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003630:Daunorubicin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D013329:Structure-Activity Relationship
D018943:Anthracyclines; D000970:Antineoplastic Agents; D006845:Hydrocarbons, Fluorinated; D003630:Daunorubicin