Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 512-521

  Carvalho, Samir A ^a,b   Feitosa, Larisse O ^a   Soares, Márcio ^a   Costa, Thadeu E M M ^a   Henriques, Maria G ^a   Salomão, Kelly ^a   De Castro, Solange L ^a   Kaiser, Marcel ^c   Brun, Reto ^c   Wardell, James L ^a   Wardell, Solange M S V ^d   Trossini, Gustavo H G ^e   Andricopulo, Adriano D ^e   Da Silva, Edson F ^a   Fraga, Carlos A M ^b  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^d CHEMSOL   (United Kingdom)

^e UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chagas' disease; Cinnamic acid; Cruzain inhibitors; N Acylhydrazone; Trypanosoma cruzi

Indexed keywords

1 (BENZO[D][1,3]DIOXOL 5 YL) 3 ( 4 BROMOPHENYL)PROP 2 EN 1 ONE; 3 ( 1,3 BENZODIOXOL 5 YL) N' [ 4 HYDROXY 3 METHOXY 5 NITROBENZYLIDENE]ACRYLOHYDRAZIDE; 3 ( 1,3 BENZOOXOL 5 YL) N' [ 2 HYDROXYBENZYLIDENE]ACRYLOHYDRAZIDE; 3 ( 3,4 DIMETHOXY 5 NITROPHENYL) N' [ 2 HYDROXYBENZYLIDENE]ACRYLOHYDRAZIDE; 3 ( 3,4 DIMETHOXY 5 NITROPHENYL) N' [ 4 HYDROXY 3 METHOXY 5 NITROBENZYLIDENE]ACRYLOHYDRAZIDE; 3 ( 3,4 DIMETHOXYPHENYL) N' [( 2 HYDROXYBENZYLIDENE)]ACRYLOHYDRAZIDE; 3 ( 3,4 DIMETHOXYPHENYL) N' [( 4 HYDROXY 3 METHOXY 5 NITROBENZYLIDENE)]ACRYLOHYDRAZIDE; 3 HYDROXY N' (( 2 HYDROXYNAPHTHALEN 1 YL)METHYLENE) 7 METHOXY 2 NAPHTHOHYDRAZIDE; ANTITRYPANOSOMAL AGENT; BENZNIDAZOLE; CYSTEINE PROTEINASE INHIBITOR; HYDRAZONE DERIVATIVE; N' ( 2 HYDROXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 3 HYDROXY 4 METHOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 3,4 DIHYDROXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 3,4 DIMETHOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 3,4 METHYLENEDIOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 3,4,5 TRIMETHOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 BROMOBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 CHLOROBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 FLUOROBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 HYDROXY 3 METHOXY 5 NITROBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 HYDROXY 3 METHOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 HYDROXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 METHOXYBENZYLIDENE)CINNAMOHYDRAZIDE; N' ( 4 NITROBENZYLIDENE)CINNAMOHYDRAZIDE; N' [ 2 HYDROXYBENZYLIDENE] 3 ( 3,4,5 TRIMETHOXYPHENYL)ACRYLOHYDRAZIDE; N' [ 4 HYDROXY 3 METHOXY 5 NITROBENZYLIDENE] 3 ( 3,4,5 TRIMETHOXYPHENYL)ACRYLOHYDRAZIDE; N' BENZYLIDENECINNAMOHYDRAZIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMASTIGOTE; ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONFORMATION; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MOLECULAR HYBRIDIZATION; NONHUMAN; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE;

ANIMALS; CELL LINE; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; CINNAMATES; CYSTEINE ENDOPEPTIDASES; DRUG DESIGN; HYDRAZONES; INHIBITORY CONCENTRATION 50; MICE; PROTOZOAN PROTEINS; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

EID: 84864406333     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.05.041     Document Type: Article

References (40)

1. WHO First WHO Report on Neglected Tropical Diseases: Working to Overcome the Global Impact of Neglected Tropical Diseases. Geneva, Switzerland 2010 World Health Organization Geneva (WHO/HTM/NTD/2010.1)
2. A. Rassi Jr., A. Rassi, and J.A. Marin-Neto Chagas disease Lancet 375 2010 1388 1402
3. G.A. Schmunis Epidemiology of Chagas disease in non-endemic countries: the role of international migration Mem. Inst. Oswaldo Cruz 102 2007 75 85 (Pubitemid 350146006)
4. M.N.C. Soeiro, and S.L. deCastro Screening of potential anti-Trypanosoma cruzi candidates: in vitro and in vivo studies Open Med. Chem. J. 5 2011 21 30
5. J.J. Cazzulo, V. Stoka, and V. Turk The major cysteine proteinase of Trypanosoma cruzi: a valid target for chemotherapy of Chagas disease Curr. Pharm. Des. 7 2001 1143 1156 (Pubitemid 32640574)
6. J.C. Engel, I. Hsieh, and J.H. McKerrow Cysteine protease inhibitors cure an experimental Trypanosoma cruzi infection J. Exp. Med. 188 1998 725 734 (Pubitemid 28387935)
7. S.C. Barr, K.L. Warner, B.G. Kornreic, J. Piscitelli, A. Wolfe, L. Benet, and J.H. McKerrow A cysteine protease inhibitor protects dogs from cardiac damage during infection by Trypanosoma cruzi Antimicrob. Agents Chemother. 49 2005 5160 5161 (Pubitemid 41778941)
8. M. Sajid, S.A. Robertson, L.S. Brinen, and J.H. McKerrow Cruzain: the path from target validation to the clinic Adv. Exp. Med. Biol. 712 2011 100 115
9. C.D. Duarte, E.J. Barreiro, and C.A.M. Fraga Privileged structures: a useful concept for the rational design of new lead drug candidates Mini Rev. Med. Chem. 7 2007 1108 1119 (Pubitemid 350200217)
10. C.A.M. Fraga, and E.J. Barreiro Medicinal chemistry of N-acylhydrazones: new lead-compounds of analgesic, antiinflammatory and antithrombotic drugs Curr. Med. Chem. 13 2006 167 198
11. R. Li, X. Chen, B. Gong, P.M. Selzer, Z. Li, E. Davidson, G. Kurzban, R.E. Miller, E.O. Nuzum, J.H. McKerrow, R.J. Fletterick, S.A. Gillmor, C.S. Craik, I.D. Kuntz, F.E. Cohen, and G.L. Kenyon Structure-based design of parasitic protease inhibitors Bioorg. Med. Chem. 4 1996 1421 1427 (Pubitemid 26319993)
12. C.R. Rodrigues, T.M. Flaherty, C. Springer, J.H. McKerrow, and F.E. Cohen CoMFA and HQSAR of acylhydrazide cruzain inhibitors Bioorg. Med. Chem. Lett. 12 2002 1537 1541 (Pubitemid 34521930)
13. D.R. Ifa, C.R. Rodrigues, R.B. de Alencastro, C.A.M. Fraga, and E.J. Barreiro A possible molecular mechanism for the inhibition of cysteine proteases by salicylaldehyde N-acylhydrazones and related compounds J. Mol. Struct. Theochem. 505 2000 11 17
14. R. Li, G.L. Kenyon, F.E. Cohen, X. Chen, B. Gong, J.N. Dominguez, E. Davidson, G. Kurzban, R.E. Miller, E.O. Nuzum, P.J. Rosenthal, and J.H. McKerrow In vitro antimalarial activity of chalcones and their derivatives J. Med. Chem. 38 1995 5031 5037 (Pubitemid 26012258)
15. J.C. Powers, J.L. Asgian, O.D. Ekici, and K.E. James Irreversible inhibitors of serine, cysteine, and threonine proteases Chem. Rev. 102 2002 4639 4750
16. M. Sajid, and J.H. McKerrow Cysteine proteases of parasitic organisms Mol. Biochem. Parasitol. 120 2002 1 21 (Pubitemid 34159288)
17. P.V. Desai, A. Patny, Y. Sabnis, B. Tekwani, J. Gut, P. Rosenthal, A. Srivastava, and M. Avery Identification of novel parasitic cysteine protease inhibitors using virtual screening. 1. The ChemBridge database J. Med. Chem. 47 2004 6609 6615 (Pubitemid 39657322)
18. J.C. Aponte, M. Verástegui, E. Málaga, M. Zimic, M.A.J. Vaisberg, R.H. Gilman, and G.B. Hammond Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones J. Med. Chem. 51 2008 6230 6234
19. D.M. Borchhardt, A. Mascarello, L.D. Chiaradia, R.J. Nunes, G. Oliva, R.A. Yunes, and A.D. Andricopulo Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi J. Braz. Chem. Soc. 21 2010 142 150
20. E. Knoevenagel Condensation von malondiure mit aromatiachen aldehyden durch ammoniak und amine Ber. Dtsch. Chem. Ges. 31 1898 2596 2619
21. O. Doebner Synthesis of sorbic acid [translation] Chem. Ber. 33 1900 2140 2142
22. X. Zhang, M. Breslav, J. Grimm, K. Guan, A. Huang, F. Liu, C.A. Maryanoff, D. Palmer, M. Patel, Y. Qian, C. Shaw, K. Sorgi, S. Stefanick, and D. Xu A new procedure for preparation of carboxylic acid hydrazides J. Org. Chem. 67 2002 9471 9474 (Pubitemid 36033937)
23. P.C. Lima, L.M. Lima, K.C.M. Silva, P.H.O. Leda, A.L.P. Miranda, C.A.M. Fraga, and E.J. Barreiro Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole Eur. J. Med. Chem. 35 2009 187 203
24. S.A. Carvalho, E.F. da Silva, C.A.M. Fraga, S.M.S.V. Wardell, J.L. Wardell, and E.R.T. Tiekink (2E)-N'-[(E)-4-Chlorobenzylidene]-3-phenylprop-2- enohydrazide monohydrate Acta Cryst. E E66 2010 o2410 o2411
25. A.E. Kummerle, J.M. Raimundo, C.M. Leal, G.S. DaSilva, T.M. Balliano, M.A. Pereira, C.A. DeSimone, R.T. Sudo, G. Zapata-Sudo, C.A.M. Fraga, and E.J. Barreiro Studies towards the identification of putative bioactive conformation of potent vasodilator arylidene N-acylhydrazone derivatives Eur. J. Med. Chem. 44 2009 4004 4009
26. G. Palla, G. Predieri, P. Domiano, C. Vignali, and W. Turner Conformational behavior and E/Z isomerization of N-acyl- and N-aroylhydrazones Tetrahedron 42 1986 3649 3654
27. S. Nwaka, and A. Hudson Innovative lead discovery strategies for tropical diseases Nat. Rev. Drug Discov. 5 2006 941 955 (Pubitemid 44660607)
28. A.J. Romanha, S.L. DeCastro, M.N. Soeiro, J. Lannes-Vieira, I. Ribeiro, A. Talvani, B. Bourdin, B. Blum, B. Olivieri, C. Zani, C. Spadafora, E. Chiari, E. Chatelain, G. Chaves, J.E. Calzada, J.M. Bustamante, L.H. Freitas-Junior, L.I. Romero, M.T. Bahia, M. Lotrowska, M. Soares, S.G. Andrade, T. Armstrong, W. Degrave, and Z.A. Andrade Experimental in vitro and in vivo models for drug screening and development for Chagas disease Mem. Inst. Oswaldo Cruz 105 2010 233 238
29. I.A. Pearl, and D.L. Beyer Reactions of vanillin and its derived compounds. XI. Cinnamic acids derived from vanillin and its related compounds J. Org. Chem. 16 1951 216 220
30. A.R. Katritzky, M. Wang, and S. Zhang One-pot synthesis of cinnamoyl hydrazides Arkivoc 2001 19 23 (Pubitemid 38977368)
31. K. Tanaka, K. Matsuo, A. Nakanishi, T. Hatano, H. Izeki, Y. Ishida, and W. Mori Synthesis and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides Chem. Pharm. Bull. 31 1983 2810 2819 (Pubitemid 14233246)
32. A. Hasan, S. Gapil, and I. Khan Synthesis, characterization and antifungal activity of some new 5-substituted 1,3,4-oxadiazole-2-thiols Asian J. Chem. 23 2011 2007 2010
33. K.M. Khan, M. Rasheed, Z. Ullah, S. Hayat, F. Kaukab, M.I. Choudhary, Atta-ur-Rahman, and S. Perveen Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues Bioorg. Med. Chem. 11 2003 1381 1387 (Pubitemid 36293532)
34. W.O. Godtfredsen, and S. Vangedal The reaction of hydrazine with cinnamic acid derivatives Acta Chem. Scand. 9 1955 1498 1509
35. M.B. Devani, U.S. Pathak, and J.N. Sane Synthesis of some cinnamoylarylidene hydrazines Indian J. Chem. 7 1969 1198 1199
36. I. Orhan, B. Sener, T. Atici, R. Brun, R. Perozzo, and D. Tasdemir Turkish freshwater and marine macrophyte extracts show in vitro antiprotozoal activity and inhibit FabI, a key enzyme of Plasmodium falciparum fatty acid biosynthesis Phytomedicine 13 2006 388 393 (Pubitemid 44250789)
37. K. Salomão, A.P. Dantas, C.M. Borba, L.C. Campos, D.G. Machado, F.R. Aquino-Neto, and S.L. DeCastro Chemical composition and microbicidal activity of extracts from Brazilian and Bulgarian propolis Lett. Appl. Microbiol. 38 2004 87 92 (Pubitemid 38230611)
38. S.L. DeCastro, M.C. Pinto, and A.V. Pinto Screening of natural and synthetic drugs against Trypanosoma cruzi: I - establishing a structure/activity relationship Microbios 78 1994 83 90
39. M.V. Carvalho, C. Penido, A.C. Siani, L.M.M. Valente, and M.G.M.O. Henriques Investigations on the anti-inflammatory and anti-allergic activities of the leaves of Uncaria guianensis (Aublet) J. F. Gmelin Inflammopharmacology 14 2006 48 56
40. A.E. Eakin, A.A. Mills, G. Harth, J.H. McKerrow, and C.S. Craik The sequence, organization, and expression of the major cysteine protease (cruzain) from cruzi J. Biol. Chem. 267 1992 7411 7420