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  • Title: Synthesis and topoisomerase I inhibitory properties of luotonin A analogues.
    Author: Cagir A, Eisenhauer BM, Gao R, Thomas SJ, Hecht SM.
    Journal: Bioorg Med Chem; 2004 Dec 01; 12(23):6287-99. PubMed ID: 15519171.
    Abstract:
    Luotonin A, a naturally occurring pyrroloquinazolinoquinoline alkaloid, has been previously demonstrated to be a topoisomerase I poison. A number of luotonin A derivatives have now been prepared through the condensation of anthranilic acid derivatives and 1,2-dihydropyrrolo[3,4-b]quinoline-3-one in the presence of phosphorus oxychloride. When dichloromethane was used as solvent the reaction proceeded to a single product. In contrast when the reaction was carried out in tetrahydrofuran or in phosphorus oxychloride, an additional isomeric product was obtained. The luotonin A analogues were evaluated for their ability to effect stabilization of the covalent binary complex formed between human topoisomerase I and DNA, and for cytotoxicity toward a yeast strain expressing the human topoisomerase I.
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