A series of structurally simple analogues of natural topopyrone C were synthesized and tested for cytotoxic and topoisomerase I inhibitory activities. The removal of the hydroxyl groups at the 5 and 9 positions resulted in an increased cytotoxic potency and ability to stabilize topoisomerase-mediated cleavage. In addition, the results suggest that some structural features, such as the pyrone ring and a polar group in position 11, are fundamental for topoisomerase I inhibitory effect. These structural requirements are also consistent with the cytotoxic activity.

Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors / S. Dallavalle, S. Gattinoni, S. Mazzini, L. Scaglioni, L. Merlini, S. Tinelli, G. L. Beretta, F. Zunino. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - 18:4(2008 Feb 15), pp. 1484-1489.

Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors

S. Dallavalle;S. Gattinoni;S. Mazzini;L. Scaglioni;L. Merlini;
2008-02-15

Abstract

A series of structurally simple analogues of natural topopyrone C were synthesized and tested for cytotoxic and topoisomerase I inhibitory activities. The removal of the hydroxyl groups at the 5 and 9 positions resulted in an increased cytotoxic potency and ability to stabilize topoisomerase-mediated cleavage. In addition, the results suggest that some structural features, such as the pyrone ring and a polar group in position 11, are fundamental for topoisomerase I inhibitory effect. These structural requirements are also consistent with the cytotoxic activity.
Antitumor; Cytotoxic activity; Topoisomerase I; Topopyrones
Settore CHIM/06 - Chimica Organica
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/36793
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