Synthesis, Cytotoxicity and Antileishmanial Activity of Aza-stilbene derivatives
Abstract
Stilbenes are compounds found in numerous medicinal plants and food products with some known biological and even antileishmanial activity. This paper describes the preparation of Aza-stilbene derivatives and their in vitro biological activities against Leishmania species. Most of the compounds with hydroxyl groups (2a, 2b, 2d, 2e and 2f) showed interesting results against three Leishmania species tested. Compound 2f showed the best activity against intracellular forms of L. amazonensis, with IC50 of 7.48 μM, very similar when compared to reference drug Miltefosine. It not possible associate NO production with leishmanicidal activity for all aza-stilbene derivatives. It is noteworthy that none of compounds tested showed cytotoxicity against macrophages.
Full Text:
PDFReferences
http:/www.who.int/neglected_disease/en/ accessed May 2012.
M. den Boer, D. Argaw, J. Jannin, J. Alvar, Clin. Microbiol. Infect., 2011, 17:1471-1477.
http://www.who.int/leishmaniasis/en/ accessed May 2012.
S. L. Croft, K. Seifert, V. Yardley, Indian J. Med. Res, 2006, 123, 399-410.
A. K. Shukla, B. K. Singh, S. Patra, V. K. Dubey, Appl. Biochem. Biotechnol., 2010,160, 2208-2218.
M. Ameen, Clin. Exp. Dermatol., 2010, 35, 699-705.
J. Chong, A. Poutaraud, P. Hugueney, Plant Sci., 2009, 177, 143-155.
P. Jeandet , B. Delaunois , A. Aziz , D. Donnez , Y. Vasserot , S. Cordelier, E. Courot, J. Biomed. Biotechnol., 2012, doi: 10.1155/2012/579089.
J. A. Baur, D. A. Sinclair, Nat. Rev. Drug. Discovery, 2006, 5, 493-506.
S. Renaud, M. de Lorgeril, Lancet, 1992, 339, 1523-1526.
B. Catalgol, S. Batirel, Y. Taga, N.K. Ozer, Front Pharmacol., 2012, 3, 141-159.
S. Bradamante, L. Barenghi, A. Villa, Cardiovasc. Drug Rev., 2004, 22, 169-188.
L. Kedzierski, J.M Curtis, M . Kaminska, J. Jodynis-Liebert, M. Murias, Parasitol. Res., 2007, 102, 91–97.
S. Ozkoc, S. Tuncay, S. B. Delibas, C. Akisu, Parasitol. Res., 2009, 105,1139-1143.
E. J. LaVoie, and G. A. Patani, Chem. Rev., 1996, 96, 3147-3176.
N. O. Calil, G. S. G. De Carvalho, D. C. Z. Franco, A. D. Da Silva, N. R. B. Raposo, Lett. Drug Des. Discov., 2012, 9, 8-11.
F. R. Pavan, G. S. G. De Carvalho, A. D. Da Silva, C. Q. F. Leite, ScientificWorldJournal, 2011, 11, 1113-1119.
J. Mossman, Immunol. Methods, 1983, 65, 55-63.
P. A. Machado, F. F. Hilário, L. O. Carvalho, M. L. T. Silveira, R. B. Alves, R. P. Freitas, E. S. Coimbra, Chem. Biol. Drug. Des., 2012, 80, 745–751.
L. C. Green, D. A. Wagner, J. Glogwski, P. L. Skipper, J. S. Wishnok, S. R. Tannenbaun, Anal. Biochem., 1982, 126, 131-138.
E. H. Cordes, W. P. Jencks, J. Am. Chem. Soc., 1962, 84, 826-831.
N. Ebara, Bull. Chem. Soc. Jpn., 1961, 34, 1151-1158.
J. B. Stevens, U. K. Pandit, Tetrahedron, 1983, 39, 1395-1400.
N. Rani, J. R. Sharma, M. R. Manrao, Pestic. Res. J., 2006, 18, 129-132.
M. Sekiya, T. Morimoto, Chem. Pharm. Bull., 1975, 23, 2353-2357.
L .X. Cheng, J .J. Tang, H. Luo, X. L. Jin, F. Dai, J. Yang, Y. P. Qian, X. Z. Li, B. Zhou, Bioorg. Med. Chem. Lett., 2010, 20, 2417-2420.
W. Manchot, Liebigs Ann., 1912, 388, 103-135.
A. Senier, R. B. Forster, J. Chem. Soc. Trans., 1915, 107, 1168-1173.
D. M. Ritter, J. Am. Chem. Soc., 1947, 69, 46-50.D. C. Colinese, J. Chem. Soc., 1971, 5, 864-869.
F. G. Pope, J. Chem. Soc. Trans., 1908, 93, 532-537.
D. C. Colinese, J. Chem. Soc., 1971, 5, 864-869
S. J. Wadher, N. A. Karande, S. D. Sonawane, P. G. Yeole, Int. J. Chem. Tech. Res., 2009, 1, 1303-1307.
L. D. Rodrigues, Rev. Port. Farm., 1952, 2, 95-98.
A. Kocwa, M. Eckstein, Z. Walczak, Dissertationes Pharm., 1951, 3, 149-158.
G. S. G. De Carvalho, P. A. Machado, D. T. S. De Paula, E. S. Coimbra, A. D. Silva, ScientificWorldJournal., 2010, 10, 1723-1730.
M. Vermeersch, R. I. Luz, K. Tote, J. Timmermans, P. Cos, L. Maes, Antimicrob. Agents Chemother., 2009, 53, 3855-3859.
A. G. Tempone, C. M. Oliveira, R. G. S. Berlinck, Planta Med., 2011, 77, 572-585.
H. Piotrowska, M. Kucinska, M. Murias, Mutat. Res., 2012, 750, 60-82.
P. R. Machado, J. Ampuero, L. H. Guimarães, L. Villas Boas, A. T. Rocha, A. Schriefer, R. S. Sousa, A. Talhari, G. Penna, E. M. Carvalho, PLOS Negl. Trop. Dis., 2010, 4, e912.
G. Muylder, K. K. H. Ang, S. Chen, M. R. Arkin, J. C. Engel, J. H. Mckerrow, PLOS Negl. Trop. Dis., 2011, 5, e1253.
J. L. Lemesre, D. Sereno, S. Daulouède, B. Veyret, N. Brajon, P. Vincendeau, Exp. Parasitol., 1997, 86: 58-68.
R. M. Mukbel, C. P. Jr, K. Gibson, M. Ghosh, C. Petersen, D. E. Jones, Am. J. Trop. Med. Hyg., 2007, 76, 669-675.
DOI: http://dx.doi.org/10.13171/mjc.2.3.2013.07.02.16
Refbacks
- There are currently no refbacks.
Copyright (c) 2015 Mediterranean Journal of Chemistry