Browsing by Author "Fournet, A"

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    Studies on quinones. Part 38: Synthesis and leishmanicidal activity of sesquiterpene 1,4-quinones
    (PERGAMON-ELSEVIER SCIENCE LTD, 2003) Valderrama, JA; Benites, J; Cortes, M; Pessoa Mahana, H; Prina, E; Fournet, A
    The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1.4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR H-1-C-13 HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described. (C) 2003 Elsevier Ltd. All rights reserved.
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    Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones
    (PERGAMON-ELSEVIER SCIENCE LTD, 2005) Valderrama, JA; Zamorano, C; Gonzalez, MF; Prina, E; Fournet, A
    Acylhydroquinone-based compounds are attractive targets for the design of new leishmanicidal drugs. We have previously described sesquiterpene quinones and hydroquinones series, which exhibit different degree of potency against Leishmania amazonensis. The present study details the preparation of acylchloroquinones and hydroquinones possessing lipophilic substituents and examines their in vitro activity against intracellular L. amazonensis amastigotes. The quinone or hydroquinone nucleus is essential for the activity of the members of the series. The lipophilicity of the cycloaliphatic systems in these members seems to attenuate the cytotoxical effect and increases the selectivity of those compounds containing the norbornene system. (c) 2005 Elsevier Ltd. All rights reserved.
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    Synthesis and in vitro antiprotozoal activity of thiophene ring-containing quinones
    (PHARMACEUTICAL SOC JAPAN, 1999) Valderrama, J; Fournet, A; Valderrama, C; Bastias, S; Astudillo, C; de Arias, AR; Inchausti, A; Yaluff, G
    A series of quinones (3a-i, 4-9, 11) and aromatic compounds (2a, 2d, 2g) containing the thiophene ring were tested in vitro against the trypomastigote form of Trypanosoma cruzi and the promastigote forms of Leishmania. The quinones 3a-i, 4, 5a, b, 6 and 9 having the thiophene ring fused to a quinone nucleus were the most active members of the series. The electron affinities of the benzo[b]thiophene-4,7-quinones 3, evaluated by their LUMO energies and halfwave potentials, are reported.