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Leverrier, A.; Bero, J.; Frédérich, M.; Quetin-Leclercq, J.; Palermo, J. "Antiparasitic hybrids of Cinchona alkaloids and bile acids" (2013) European Journal of Medicinal Chemistry. 66:355-363
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Abstract:

A series of 16 hybrids of Cinchona alkaloids and bile acids (4a-h, 5a-h) was prepared by means of a Barton-Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC50 values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC50 ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC50 values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6-15.7. © 2013 Elsevier Masson SAS. All rights reserved.

Registro:

Documento: Artículo
Título:Antiparasitic hybrids of Cinchona alkaloids and bile acids
Autor:Leverrier, A.; Bero, J.; Frédérich, M.; Quetin-Leclercq, J.; Palermo, J.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Pab. 2, 1428 Buenos Aires, Argentina
Pharmacognosy Research Group, Louvain Drug Research Institute, Université Catholique de Louvain, Avenue E. Mounier B1.72.03, B-1200 Brussels, Belgium
Laboratory of Pharmacognosy, Drug Research Center (CIRM), University of Liège, Avenue de l'Hôpital 1, B36, B-4000 Liège, Belgium
Palabras clave:Antiparasitic activity; Barton-Zard reaction; Bile acids; Cinchona alkaloids; Hybrids; amphotericin B; antimalarial agent; antitrypanosomal agent; artemisinin; bile acid; camptothecin; Cinchona alkaloid; cinchonidine; cinchonine; quinidine; quinine; suramin; antiparasitic agent; bile acid; Cinchona alkaloid; quinoline; antiprotozoal activity; article; controlled study; cytotoxicity; decarboxylation; drug synthesis; human; human cell; IC 50; Leishmania mexicana; Plasmodium falciparum; proton nuclear magnetic resonance; proton transport; Trypanosoma brucei; antileishmanial activity; antiplasmodial activity; antitrypanosomal activity; Article; drug activity; drug cytotoxicity; drug synthesis; IC50; in vitro study; nonhuman; Plasmodium; Trypanosoma brucei brucei
Año:2013
Volumen:66
Página de inicio:355
Página de fin:363
DOI: http://dx.doi.org/10.1016/j.ejmech.2013.06.004
Título revista:European Journal of Medicinal Chemistry
Título revista abreviado:Eur. J. Med. Chem.
ISSN:02235234
CODEN:EJMCA
CAS:amphotericin B, 1397-89-3, 30652-87-0; artemisinin, 63968-64-9; camptothecin, 7689-03-4; cinchonidine, 485-71-2; cinchonine, 118-10-5; quinidine, 56-54-2; quinine, 130-89-2, 130-95-0, 14358-44-2, 549-48-4, 549-49-5, 60-93-5, 7549-43-1; suramin, 129-46-4, 145-63-1; quinoline, 91-22-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v66_n_p355_Leverrier

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Citas:

---------- APA ----------
Leverrier, A., Bero, J., Frédérich, M., Quetin-Leclercq, J. & Palermo, J. (2013) . Antiparasitic hybrids of Cinchona alkaloids and bile acids. European Journal of Medicinal Chemistry, 66, 355-363.
http://dx.doi.org/10.1016/j.ejmech.2013.06.004
---------- CHICAGO ----------
Leverrier, A., Bero, J., Frédérich, M., Quetin-Leclercq, J., Palermo, J. "Antiparasitic hybrids of Cinchona alkaloids and bile acids" . European Journal of Medicinal Chemistry 66 (2013) : 355-363.
http://dx.doi.org/10.1016/j.ejmech.2013.06.004
---------- MLA ----------
Leverrier, A., Bero, J., Frédérich, M., Quetin-Leclercq, J., Palermo, J. "Antiparasitic hybrids of Cinchona alkaloids and bile acids" . European Journal of Medicinal Chemistry, vol. 66, 2013, pp. 355-363.
http://dx.doi.org/10.1016/j.ejmech.2013.06.004
---------- VANCOUVER ----------
Leverrier, A., Bero, J., Frédérich, M., Quetin-Leclercq, J., Palermo, J. Antiparasitic hybrids of Cinchona alkaloids and bile acids. Eur. J. Med. Chem. 2013;66:355-363.
http://dx.doi.org/10.1016/j.ejmech.2013.06.004