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Toward new camptothecins. Part 4: On the reactivity of nitro and amino precursors of aza analogs of 5-methoxycarbonyl camptothecin
Authors:Laurent Gavara  Daniel Couturier  Jean-Pierre Hénichart
Institution:a Ecole des Hautes Etudes d'Ingénieur, EA 2692, 13 rue de Toul, 59046 Lille, France
b Laboratoire d'Ingéniérie Moléculaire, Université des Sciences et Technologies de Lille 1, 59655 Lille, France
c Institut de Chimie Pharmaceutique Albert Lespagnol, EA2692, Université de Lille 2, rue du Professeur Laguesse, BP 83 F-59006 Lille, France
Abstract:In the context of formation of new aza analogs of camptothecin, nitration then reduction of condensed pyridones was realized, leading to new derivatives of pyrrolo-aza-indoles. Treatment of these compounds with hydrobromic acid led to new structure rearrangements while oxidation of the α-position was unsuccessful. Mechanisms of formation of the new products are discussed.
Keywords:2-Pyridone  Camptothecin  Decarboxylation  Nitro displacement
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