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1 Polish Journal of Chemistry

1 2004

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Rational Design, synthesis and Biological Evaluation of 3H-Naphtho[1,2,3-de]quinoline-2,7-diones: a New Class of Potential Antitumor Agents

Antonini L., Polucci P., Magnano A., Sparapani S., Martelli S.

Polish Journal of Chemistry

2004

Vol. 78 / nr 8

1019-1025

A series of novel potential DNA-binding antitumor agents, 6-[(_-aminoalkyl)amino]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones 3a-j, has been prepared by nucleophilic substitution of commercially available 6-bromo-4-methyl-1-phenyl-3Hnaphtho[ 1,2,3-de]quinoline-2,7-dione with the suitable 1-[_-(alkylamino)alkyl]amine. In vitro cytotoxic potencies of these derivatives toward six tumor cell lines, including human colon adenocarcinoma (HT29) and human ovarian carcinoma (A2780 sensitive, A2780cisR cisplatin-resistant, CH1, CH1cisR cisplatin-resistant, and SKOV-3), are described and compared to that of reference drugs. The 6-[3-(diethylamino)propyl]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones (3e), which possesses good cytotoxicity and low or none cross resistance with Cs on resistant cell lines, can be regarded as a new lead in the development of intercalating anticancer derivatives.