Preparation of 5-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyloxy)-6-hydroxynap htho[2,3- f]quinoline-7,12-dione (FT-Alz), a new-type, potentially antitumor substance with various biological activities.
The title compound (6), its structure being imaginatively created, has been prepared through coupling of alizarine blue (2), a classical dye, and 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (3). Compound 6 has considerably higher and different antitumor activity from that of doxorubicin or its analogue (10), and, further, has properties to reverse multidrug resistance (by P-glycoprotein), to inhibit topoisomerase II, and to induce apoptosis.
Tsuchiya
T
T
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Takagi
Y
Y
Yamada
H
H
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
C405604:5-(2,6-dideoxy-2-fluorotalopyranosyloxy)-6-hydroxynaphtho(2,3-f)quinoline-7,12-dione; D000970:Antineoplastic Agents; D006027:Glycosides; D009285:Naphthoquinones