Antiparasitic hybrids of Cinchona alkaloids and bile acids

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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 ne...

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Autor principal: Leverrier, A.
Otros Autores: Bero, J., Frédérich, M., Quetin-Leclercq, J., Palermo, J.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier Masson SAS 2013
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 cas  |a 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 
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100 1 |a Leverrier, A. 
245 1 0 |a Antiparasitic hybrids of Cinchona alkaloids and bile acids 
260 |b Elsevier Masson SAS  |c 2013 
270 1 0 |m Palermo, J.; Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Pab. 2, 1428 Buenos Aires, Argentina; email: palermo@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a WHO/factsheets, , www.who.int 
504 |a Michael, J.P., (2008) Nat. Prod. Rep., 25, pp. 166-187 
504 |a Kaur, K., Reddy, R.P., Jain, R., (2010) Eur. J. Med. Chem., 45, pp. 3245-3264 
504 |a Loiseau, P.M., Gupta, S., Verma, A., Srivastava, S., Puri, S.K., Sliman, F., Normand-Bayle, M., Desmaele, D., (2011) Antimicrob. Agents Chemother., 55, pp. 1777-1780 
504 |a Fournet, A., Barrios, A.A., Muñoz, V., Hocquemiller, R., Cavé, A., Bruneton, J., (1993) Antimicrob. Agents Chemother., 37, pp. 859-863 
504 |a Fakhfakh, M.A., Fournet, A., Prina, E., Mouscadet, J.-F., Franck, X., Hocquemiller, R., Figadère, B., (2003) Bioorg. Med. Chem., 11, pp. 5013-5023 
504 |a Tietze, L.F., Bell, H.P., Chandrasekhar, S., (2003) Angew. Chem. Int. Ed., 42, pp. 3996-4028 
504 |a Walsh, J.J., Coughlan, D., Heneghan, N., Gaynora, C., Bell, A., (2007) Bioorg. Med. Chem. Lett., 17, pp. 3599-3602 
504 |a Antinarelli, L.M.R., Carmo, A.M.L., Pavan, F.R., Queico, C., Leite, F., Da Silva, A.D., Coimbra, E.S., Salunke, D.B., (2012) Org. Med. Chem. Lett., 2, p. 16. , Provisional pdf 
504 |a Mehta, G., Singh, V., (2002) Chem. Soc. Rev., 31, pp. 324-334 
504 |a Corrales, R.C.N.R., De Souza, N.B., Pinheiro, L.S., Abramo, C., Coimbra, E.S., Da Silva, A.D., (2011) Biomed. Pharmacother., 65, pp. 198-203 
504 |a Sievänen, E., (2007) Molecules, 12, pp. 1859-1889 
504 |a Bhat, L., Jandeleit, B., Dias, T.M., Moors, T.L., Gallop, M.A., (2005) Bioorg. Med. Chem. Lett., 15, pp. 85-87 
504 |a Bero, J., Frédérich, M., Quetin-Leclercq, J., (2009) J. Pharm. Pharmacol., 61, pp. 1401-1433 
504 |a Siless, G.E., Knott, M.E., Derita, M.G., Zacchino, S.A., Puricelli, L., Palermo, J.A., (2012) Steroids, 77, pp. 45-51 
504 |a Saraiva, M.F., Couri, M.R.C., Le Hyaric, M., De Almeida, M.V., (2009) Tetrahedron, 65, pp. 3563-3572 
504 |a Togo, H., 5-Alkylation of aromatics (2004) Adv. Free Radic. React. Org. Synth., pp. 157-170 
504 |a Yardley, J.P., Bright, R.E., Rane, L., Rees, R.W.A., Russel, P.B., Smith, H., (1971) J. Med. Chem., 14, pp. 62-65 
504 |a Johansson, C.C.C., Bremeyer, N., Ley, S.V., Owen, D.R., Smith, S.C., Gaunt, M.J., (2006) Angew. Chem. Int. Ed., 45, pp. 6024-6028 
504 |a Barton, D.H.R., Garcia, B., Togo, H., Zard, S.Z., (1986) Tetrahedron Lett., 27, pp. 1327-1330 
504 |a Castagino, E., Corsano, S., Barton, D.H.R., Zard, S.Z., (1986) Tetrahedron Lett., 27, pp. 6337-6338 
504 |a Barton, D.H.R., Jaszberenyl, J.Cs., Tang, D., (1993) Tetrahedron Lett., 34, pp. 3381-3384 
504 |a Pink, R., Hudson, A., Mouriès, M.A., Bendig, M., (2005) Nat. Rev. Drug Discov., 4, pp. 727-740 
504 |a Hirumi, H., Hirumi, K., (1994) Parasitol. Today, 10, pp. 80-84 
504 |a Brun, R., Lun, Z.R., (1994) Vet. Parasitol., 52, pp. 37-46 
504 |a Trager, W., Jensen, J.B., (1976) Science, 193, pp. 673-675 
504 |a Hoet, S., Opperdoes, F., Brun, R., Adjakidje, V., Quetin-Leclercq, J., (2004) J. Ethnopharmacol., 91, pp. 37-42 
504 |a Hoet, S., Stevigny, C., Block, S., Opperdoes, F., Colson, P., Baldeyrou, B., Lansiaux, A., Quetin-Leclercq, J., (2004) Planta Med., 70, pp. 407-413 
504 |a Makler, M.T., Ries, J.M., Williams, J.A., Bancroft, J.E., Piper, R.C., Gibbins, B.L., Hinrichs, D.J., (1993) Am. J. Trop. Med. Hyg., 48, pp. 739-741 
504 |a Murebwayire, S., Frederich, M., Hannaert, V., Jonville, M.C., Duez, P., (2008) Phytomedicine, 15, pp. 728-733 
504 |a Stevigny, C., Block, S., Pauw-Gillet, M.C., De Hoffmann, E., Llabres, G., Adjakidje, V., Quetin-Leclercq, J., (2002) Planta Med., 68, pp. 1042-1044 
504 |a Mosmann, T., (1983) J. Immunol. Methods, 65, pp. 55-63 
520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Secretaría de Ciencia y Técnica, Universidad de Buenos Aires, 20020100100123 
536 |a Detalles de la financiación: Applied Scientific Research Fund, N° 3.4533.10 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP No. 516-2009 
536 |a Detalles de la financiación: Research at the University of Buenos Aires was supported by Grants from CONICET (PIP No. 516-2009), UBACYT (20020100100123, Prog. 2011–2014), and ANPCYT (PICT 2010-1808). A.L. thanks CONICET for a postdoctoral fellowship. This work was partly supported by the Belgian Fund for Scientific Research (grant N° 3.4533.10 ). Appendix A 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Pab. 2, 1428 Buenos Aires, Argentina 
593 |a Pharmacognosy Research Group, Louvain Drug Research Institute, Université Catholique de Louvain, Avenue E. Mounier B1.72.03, B-1200 Brussels, Belgium 
593 |a Laboratory of Pharmacognosy, Drug Research Center (CIRM), University of Liège, Avenue de l'Hôpital 1, B36, B-4000 Liège, Belgium 
690 1 0 |a ANTIPARASITIC ACTIVITY 
690 1 0 |a BARTON-ZARD REACTION 
690 1 0 |a BILE ACIDS 
690 1 0 |a CINCHONA ALKALOIDS 
690 1 0 |a HYBRIDS 
690 1 0 |a AMPHOTERICIN B 
690 1 0 |a ANTIMALARIAL AGENT 
690 1 0 |a ANTITRYPANOSOMAL AGENT 
690 1 0 |a ARTEMISININ 
690 1 0 |a BILE ACID 
690 1 0 |a CAMPTOTHECIN 
690 1 0 |a CINCHONA ALKALOID 
690 1 0 |a CINCHONIDINE 
690 1 0 |a CINCHONINE 
690 1 0 |a QUINIDINE 
690 1 0 |a QUININE 
690 1 0 |a SURAMIN 
690 1 0 |a ANTIPARASITIC AGENT 
690 1 0 |a BILE ACID 
690 1 0 |a CINCHONA ALKALOID 
690 1 0 |a QUINOLINE 
690 1 0 |a ANTIPROTOZOAL ACTIVITY 
690 1 0 |a ARTICLE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a CYTOTOXICITY 
690 1 0 |a DECARBOXYLATION 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a HUMAN 
690 1 0 |a HUMAN CELL 
690 1 0 |a IC 50 
690 1 0 |a LEISHMANIA MEXICANA 
690 1 0 |a PLASMODIUM FALCIPARUM 
690 1 0 |a PROTON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a PROTON TRANSPORT 
690 1 0 |a TRYPANOSOMA BRUCEI 
690 1 0 |a ANTILEISHMANIAL ACTIVITY 
690 1 0 |a ANTIPLASMODIAL ACTIVITY 
690 1 0 |a ANTITRYPANOSOMAL ACTIVITY 
690 1 0 |a ARTICLE 
690 1 0 |a DRUG ACTIVITY 
690 1 0 |a DRUG CYTOTOXICITY 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a IC50 
690 1 0 |a IN VITRO STUDY 
690 1 0 |a NONHUMAN 
690 1 0 |a PLASMODIUM 
690 1 0 |a TRYPANOSOMA BRUCEI BRUCEI 
700 1 |a Bero, J. 
700 1 |a Frédérich, M. 
700 1 |a Quetin-Leclercq, J. 
700 1 |a Palermo, J. 
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