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

T Tsuchiya; Y Takagi; H Yamada

doi:10.1016/s0960-894x(99)00655-1

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

Bioorg Med Chem Lett. 2000 Feb 7;10(3):203-7. doi: 10.1016/s0960-894x(99)00655-1.

Authors

T Tsuchiya¹, Y Takagi, H Yamada

Affiliation

¹ Institute of Bioorganic Chemistry, Kawasaki, Japan.

PMID: 10698436
DOI: 10.1016/s0960-894x(99)00655-1

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Drug Screening Assays, Antitumor
Glycosides / chemical synthesis*
Glycosides / pharmacology
Mice
Naphthoquinones / chemical synthesis*
Naphthoquinones / pharmacology
Tumor Cells, Cultured

Substances

5-(2,6-dideoxy-2-fluorotalopyranosyloxy)-6-hydroxynaphtho(2,3-f)quinoline-7,12-dione
Antineoplastic Agents
Glycosides
Naphthoquinones