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Synthesis of 6-Dialkylaminoalkylamino Pyrano[2,3-c]Acridones and Benzo[b]Pyrano[3,2-h]Acridones: Soluble Acronycine Analogues With Increased Cytotoxic Activity

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Abstract:



The novel 6-dialkylaminoalkylamino-3,3,12-trimethyl-3,12-dihydro-7H-pyrano[2,3-c ]acridine-7-ones 5–11 and their benzo [b]pyrano[2,3-h]acridine-7-one counterparts 12–18 were prepared by treatment of acronycine (1) or benzo[b]acronycine (4) with an excess of the appropriate dialkylaminoalkylamine. In both series, the introduction of a dialkylaminoalkylamino side chain at position 6 resulted in a significant increase of the cytotoxic activity against L1210 cells when compared with the parent compounds bearing a methoxy group, accompanied with an increased potency to arrest cells in the G2 + M phases of the cell cycle.

Keywords: Key words: Acronycine; Benzo[b]acronycine; 6-Dialkylaminoalkylamino side chains; Cytotoxicity

Document Type: Research Article

DOI: https://doi.org/10.3727/096504002108748222

Affiliations: 1: *Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. No. 8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, F-75006 Paris, France 2: †Laboratoire de Pharmacognosie de l'Université de Rouen-Haute Normandie, Faculté de Pharmacie, 22, Boulevard Gambetta, F-76183 Rouen Cedex, France 3: ‡Les Laboratoires Servier, 1 rue Carle Hébert, F-92415 Courbevoie Cedex, France 4: §Institut de Recherche Servier, 11 rue des Moulineaux, F-92150 Suresnes, France

Publication date: 2002-01-01

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