The electrochemistry of antineoplastic furanquinones: Electrochemical properties of benzo[ b]naphtho[2,3- d]furan-6,11-dione derivatives

• Published in: Electrochimica acta Vol. 41; no. 15; pp. 2399 - 2403
• Main Authors: Crawford, P.W., Carlos, E., Ellegood, J.C., Cheng, C.C., Dong, Q., Liu, D.F., Luo, Y.L.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 1996; Elsevier
• Subjects: 11-dione; [23-d]furan-6; benzo[ b]naphtho; Chemistry; cyclic voltammetry; Electrochemistry; Exact sciences and technology; furanquinone; General and physical chemistry; inhibitory activity; Kinetics and mechanism of reactions; reduction; reduction potentials; [23-d]furan-6; 11-dione; benzo[ b]naphtho; cyclic voltammetry; reduction potentials; inhibitory activity; reduction; furanquinone; Antineoplastic agent; Cell proliferation; ECE mechanism; Physicochemical properties activity relationship; Oxygen heterocycle; Chemical reduction; Platinum; Aromatic compound; Inhibition; Electrochemical reaction; Aprotic solvent; Tumor cell; Organic compounds; Quinone; Transition metal; Reduction potential; Tetracyclic compound; Experimental study; In vitro; Biological activity; HL60 cell line; Organic solvent; N,N-Dimethylformamide; Phenols; Property structure relationship; Disk electrode
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/0013-4686(96)00020-5

The electrochemical reductions of 9 benzo[
b]naphtho[2,3-
d]furan-6,11-dione derivatives in dimethylformamide were investigated. In the aprotic medium the quinones reduced in two successive one-electron steps. The influence of molecular structure on reduction potential is addressed. The reduction process involved a single irreversible two-electron process in the presence of a proton source, occurring
via an ECE mechanism. A relationship is observed between reduction potential and reported inhibitory activity against various cancer cell lines. The hydroxyl substituted derivatives exhibit the most positive
E
1
2
values and have generally more potent activities.