In vitro antischistosomal evaluation of some newly synthesized praziquantel derivatives

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• 作者：M. M. Kamel (1)
  M. M. Anwar (1)
  A. M. Soliman (1)
  H. F. Abdel-Hamid (2)
  
• 关键词：Praziquantel ; Arylidene derivatives ; Mannich bases ; Antischistosomal evaluation ; Schistosoma mansoni
• 刊名：Research on Chemical Intermediates
• 出版年：2013
• 出版时间：September 2013
• 年：2013
• 卷：39
• 期：7
• 页码：3417-3426
• 全文大小：228KB
• 参考文献：1. J. Keiser, J. Utzinger, Advances in the discovery and development of trematocidal drugs. Expert Opin. Drug Discov. 2(S1), S9–S23 (2007) CrossRef
  2. G.B.F. Carvalho, R.A. da Silva Pereira, L.G.G. Pacífico, C.T. Fonseca, Identification of / Schistosoma mansoni candidate antigens for diagnosis of schistosomiasis. Mem. Inst. Oswaldo Cruz 106, 837-43 (2011) CrossRef
  3. L.A.L. Quezada, J.H. McKerrow, / Schistosome serine protease inhibitors: parasite defense or homeostasis? An. Acad. Bras. Ciênc. 83, 663-72 (2011) CrossRef
  4. J. Utzinger, J. Keiser, Schistosomiasis and soil-transmitted helminthiasis: common drugs for treatment and control. Expert Opin. Pharmacother. 5, 263-85 (2004) CrossRef
  5. M.J. van der Werf, S.J. de Vlas, S. Brooker, C.W.N. Looman, N.J.D. Nagelkerke, J.D.F. Habbema, D. Engels, Quantification of clinical morbidity associated with / schistosome infection in sub-Saharan Africa. Acta Trop. 86, 125-39 (2003) CrossRef
  6. A. Fenwick, J.P. Webster, Schistosomiasis: challenges for control, treatment and drug resistance. Curr. Opin. Infect. Dis. 19, 577-82 (2006) CrossRef
  7. M.J. Doenhoff, L. Pica-Mattoccia, Praziquantel for the treatment of schistosomiasis: its use for control in areas with endemic disease and prospects for drug resistance. Expert Rev. Anti Infect. Ther. 4, 199-10 (2006) CrossRef
  8. R. G?nnert, P. Andrews, Praziquantel, a new broad-spectrum antischistosomal agent. Z. Parasitenk. 52, 129-50 (1977) CrossRef
  9. B.L. Blas, M.I. Rosales, I.L. Lipayon, K. Yasuraoka, H. Matsuda, M. Hayashi, The schistosomiasis problem in the Philippines: a review. Parasitol. Int. 53, 127-34 (2004) CrossRef
  10. V.R. Southgate, D. Rollinson, L.A. Tchuem Tchuenté, P. Hagan, Towards control of schistosomiasis in sub-Saharan Africa. J. Helminthol. 79, 181-85 (2005) CrossRef
  11. C.M.S. Menezes, G. Rivera, M.A. Alves, D.N. do Amaral, J.P.B. Thibaut, F. No?l, E.J. Barreiro, L.M. Lima, Synthesis, biological evaluation, and structure–activity relationship of clonazepam, meclonazepam, and 1,4-benzodiazepine compounds with schistosomicidal activity. Chem. Biol. Drug Des. 79, 943-49 (2012) CrossRef
  12. S.-H. Xiao, J.-Y. Mei, P-Y Jiao, The in vitro effect of mefloquine and praziquantel against juvenile and adult / Schistosoma japonicum. Parasitol. Res. 106(1), 237-46 (2009) CrossRef
  13. S. Botros, J. Bennett, Praziquantel resistance. Expert Opin. Drug Discov. 2, 535-40 (2007) CrossRef
  14. Y.S. Liang, J.I. Bruce, D.A. Boy, Laboratory cultivation of / schistosome vector snails and maintenance of / schistosome life cycle. Proc. First Sino-American Symp. 1, 34-8 (1987)
  15. R.H. Duvall, W.B. DeWitt, An improved perfusion technique for recovering adult schistosomes from laboratory animals. Am. J. Trop. Med. Hyg. 16, 483-86 (1967)
  16. J. Vaya, P.A. Belinky, M. Aviram, Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. Free Radic. Biol. Med. 23(2), 302-13 (1997) CrossRef
  17. M. Larsen, H. Kromann, A. Kharazmi, S.F. Nielsen, Conformationally restricted anti-plasmodial chalcones. Bioorg. Med. Chem. Lett. 15(21), 4858-861 (2005) CrossRef
  18. S.F. Nielsen, T. Boesen, M. Larsen, K. Sch?nning, H. Kromann, Antibacterial chalcones–bioisosteric replacement of the 4-hydroxy group. Bioorg. Med. Chem. 12(11), 3047-054 (2004) CrossRef
  19. M. Chen, S.B. Christensen, L. Zhai, M. Rasmussen, T.G. Theander, S. Fr?kj?r, B. Steffansen, J. Davidsen, A. Kharazmi, The novel oxygenated chalcone 2,4 dimethyloxy-4-butoxychalcone, exhibits potent activity against human malaria parasite / Plasmodium falciparum in vitro and rodnet parasites / Plasmodium berghei and / Plasmodium yoelii in vivo. J. Infect. Dis. 176, 1327-333 (1997) CrossRef
  20. L. Zhai, M. Chen, J. Blom, T.G. Theander, S.B. Christensen, A. Kharazmi, The antileishmanial activity of novel oxygenated chalcones and their mechanism of action. J. Antimicrob. Chemother. 43, 793-03 (1999) CrossRef
  21. D. Binder, C.R. Noe, W. Holzer, B. Rosenwirth, Thiophene as a structural element of physiologically active compounds, XII: thiophene analogues of antiviral chalcones. Arch. Pharm. 318, 48-9 (1985) CrossRef
  22. J. Shen, H. Wang, H. Liu, Y. Sun, Z. Liu, Br?nsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone. J. Mol. Catal. A: Chem. 280, 24-8 (2008) CrossRef
  23. B.M. Kotecka, G.B. Barlin, M.D. Edstein, K.H. Rieckmann, New quinoline di-mannich base compounds with greater antimalarial activity than chloroquine, amodiaquine, or pyronaridine. Antimicrob. Agents Chemother. 41(6), 1369-374 (1997)
  24. A.S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz, M.A. EL-Gendy, Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents. Bioorg. Med. Chem. 14, 1236-246 (2006) CrossRef
  25. M.A. Ali, M. Shaharyar, Oxadiazole mannich bases: synthesis and antimycobacterial activity. Bioorg. Med. Chem. 17, 3314-316 (2007) CrossRef
  26. D. Sriram, D. Banerjee, P. Yogeeswari, Efavirenz Mannich bases: synthesis, anti-HIV and antitubercular activities. J. Enzyme Inhib. Med. Chem. 24, 1- (2009) CrossRef
  27. M.M. Kamel, M. Nasr, New styrylquinolines of expected antimalarial activity. Pharmazie 34, 440-41 (1979)
  28. M.G.R. Pitta, A.C.A. Silva, J.K.A.L. Neves, P.G. Silva, J.I. Irm?o, E. Malague?o, J.V. Santana, M.C.A. Lima, S.L. Galdino, I.R. Pitta, M.C.P.A. Albuquerque, New imidazolidinic bioisosters: potential candidates for antischistosomal drugs. Mem. Inst. Oswaldo Cruz 101, 313-16 (2006) CrossRef
  
• 作者单位：M. M. Kamel (1)
  M. M. Anwar (1)
  A. M. Soliman (1)
  H. F. Abdel-Hamid (2)
  
  1. Therapeutical Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
  2. Chemistry of Pesticides Department, National Research Centre, Dokki, Cairo, Egypt
  

文摘

Praziquantel, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one, was used as the parent starting material to synthesize a new series of praziquantel-3-arylidene derivatives 1a–c and praziquantel–Mannich bases 2a–d, hoping to obtain new antischistosomal compounds of more activity and lower adverse effects. The antischistosomal activity of the newly synthesized compounds was evaluated using in vitro Schistosoma mansoni worm killing tests. Both compounds 2c and 2d exhibited significant in vitro antischistosomal activity and may offer promising use as an antischistosomal drug either alone or in combination with praziquantel.