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Volumn 52, Issue 13, 2009, Pages 4038-4053

Synthesis and electrochemistry of 2-ethenyl and 2-ethanyl derivatives of 5-nitroimidazole and antimicrobial activity against Giardia lamblia

Author keywords

[No Author keywords available]

Indexed keywords

1 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 2 (4 METHYLPHENYL)ETHANE 1,2 DIYL DIACETATE; 1 (4 BROMOPHENYL) 2 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL)ETHANE 1,2 DIOL; 1 METHYL 2 [2 (1 METHYL 1H IMIDAZOL 2 YL)VINYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 2 [2 (2 METHYLPHENYL)VINYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 2 [2 (2,4,6 TRIMETHYLPHENYL)VINYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 2 [2 (3 METHYLPHENYL)VINYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 2 [2 (4 METHYLPHENYL)VINYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 2 [2 (4METHYLPHENYL)ETHYL] 5 NITRO 1H IMIDAZOLE; 1 METHYL 5 NITRO 2 (2 PHENYLETHYL) 1H IMIDAZOLE; 1 METHYL 5 NITRO 2 (2 PHENYLVINYL) 1H IMIDAZOLE; 1 METHYL 5 NITRO 2 [2 (3 THIENYL)VINYL] 1H IMIDAZOLE; 1 METHYL 5 NITRO 2 [2 [4 (TRIFLUOROMETHOXY)PHENYL]VINYL] 1H IMIDAZOLE; 2 (2 BIPHENYL 2 YLVINYL) 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (2 BROMOPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (2 CHLOROPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (2 FURYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (2 IODOPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (2,4 DICHLOROPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3 BROMOPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3 CHLOROPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3 FLUOROPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3 IODOPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3 METHOXYPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (3A,7A DIHYDRO 1,3 BENZODIOXOL 5 YL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (4 BROMOPHENYL)ETHYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (4 BROMOPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 2 [2 (4 CHLOROPHENYL)VINYL] 1 METHYL 5 NITRO 1H IMIDAZOLE; 5 NITROIMIDAZOLE DERIVATIVE; METRONIDAZOLE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 67649983429     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900356n     Document Type: Article
Times cited : (81)

References (36)
  • 1
    • 33746341793 scopus 로고    scopus 로고
    • An updated review on Cryptosporidium and Giardia
    • viii
    • Huang, D. B.; White, A. C. An updated review on Cryptosporidium and Giardia. Gastroenterol. Clin. North Am. 2006, 35, 291-314, viii.
    • (2006) Gastroenterol. Clin. North Am , vol.35 , pp. 291-314
    • Huang, D.B.1    White, A.C.2
  • 2
    • 0033678745 scopus 로고    scopus 로고
    • Giardiasis as a re-emerging infectious disease and its zoonotic potential
    • Thompson, R. C. Giardiasis as a re-emerging infectious disease and its zoonotic potential. Int. J. Parasitol. 2000, 30, 1259-1267.
    • (2000) Int. J. Parasitol , vol.30 , pp. 1259-1267
    • Thompson, R.C.1
  • 3
    • 0036364352 scopus 로고    scopus 로고
    • Surface antigenic variation in Giardia lamblia
    • Nash, T. E. Surface antigenic variation in Giardia lamblia. Mol. Microbiol. 2002, 45, 585-590.
    • (2002) Mol. Microbiol , vol.45 , pp. 585-590
    • Nash, T.E.1
  • 4
    • 0037116835 scopus 로고    scopus 로고
    • Effects of stunting, diarrhoeal disease, and parasitic infection during infancy on cognition in late childhood: A follow-up study
    • Berkman, D. S.; Lescano, A. G.; Gilman, R. H.; Lopez, S. L.; Black, M. M. Effects of stunting, diarrhoeal disease, and parasitic infection during infancy on cognition in late childhood: a follow-up study. Lancet 2002, 359, 564-571.
    • (2002) Lancet , vol.359 , pp. 564-571
    • Berkman, D.S.1    Lescano, A.G.2    Gilman, R.H.3    Lopez, S.L.4    Black, M.M.5
  • 5
    • 36049034295 scopus 로고    scopus 로고
    • Persisting symptoms and duodenal inflammation related to Giardia duodenalis infection
    • Hanevik, K.; Hausken, T.; Morken, M. H.; Strand, E. A.; Morch, K.; et al. Persisting symptoms and duodenal inflammation related to Giardia duodenalis infection. J. Infect. 2007, 55, 524-530.
    • (2007) J. Infect , vol.55 , pp. 524-530
    • Hanevik, K.1    Hausken, T.2    Morken, M.H.3    Strand, E.A.4    Morch, K.5
  • 6
    • 51149116819 scopus 로고    scopus 로고
    • Pathophysiology of enteric infections with Giardia duodenalis
    • Buret, A. G. Pathophysiology of enteric infections with Giardia duodenalis. Parasite 2008, 15, 261-265.
    • (2008) Parasite , vol.15 , pp. 261-265
    • Buret, A.G.1
  • 7
    • 34047171235 scopus 로고    scopus 로고
    • Effect of chronic Giardia lamblia infection on epithelial transport and barrier function in human duodenum
    • Troeger, H.; Epple, H. J.; Schneider, T.; Wahnschaffe, U.; Ullrich, R.; et al. Effect of chronic Giardia lamblia infection on epithelial transport and barrier function in human duodenum. Gut 2007, 56, 328-335.
    • (2007) Gut , vol.56 , pp. 328-335
    • Troeger, H.1    Epple, H.J.2    Schneider, T.3    Wahnschaffe, U.4    Ullrich, R.5
  • 8
    • 0031951026 scopus 로고    scopus 로고
    • Late incidence of cancer after metronidazole use: A matched metronidazole user/nonuser study
    • Falagas, M. E.; Walker, A. M.; Jick, H.; Ruthazer, R.; Griffith, J.; et al. Late incidence of cancer after metronidazole use: a matched metronidazole user/nonuser study. Clin. Infect. Dis. 1998, 26, 384-388.
    • (1998) Clin. Infect. Dis , vol.26 , pp. 384-388
    • Falagas, M.E.1    Walker, A.M.2    Jick, H.3    Ruthazer, R.4    Griffith, J.5
  • 10
    • 34548345811 scopus 로고    scopus 로고
    • Anderson, V. R.; Curran, M. P. Nitazoxanide: a review of its use in the treatment of gastrointestinal infections. Drugs 2007, 67, 1947-1967.
    • Anderson, V. R.; Curran, M. P. Nitazoxanide: a review of its use in the treatment of gastrointestinal infections. Drugs 2007, 67, 1947-1967.
  • 11
    • 0027522732 scopus 로고
    • Nitroimidazole drugs - action and resistance mechanisms. I. Mechanisms of action
    • Edwards, D. I. Nitroimidazole drugs - action and resistance mechanisms. I. Mechanisms of action. J. Antimicrob. Chemother. 1993, 31, 9-20.
    • (1993) J. Antimicrob. Chemother , vol.31 , pp. 9-20
    • Edwards, D.I.1
  • 12
    • 0034011325 scopus 로고    scopus 로고
    • Inhibition of pyruvate-ferredoxin oxidoreductase gene expression in Giardia lamblia by a virus-mediated hammerhead ribozyme
    • Dan, M.; Wang, A. L.; Wang, C. C. Inhibition of pyruvate-ferredoxin oxidoreductase gene expression in Giardia lamblia by a virus-mediated hammerhead ribozyme. Mol. Microbiol. 2000, 36, 447-456.
    • (2000) Mol. Microbiol , vol.36 , pp. 447-456
    • Dan, M.1    Wang, A.L.2    Wang, C.C.3
  • 13
    • 0030221888 scopus 로고    scopus 로고
    • Characterisation and purification of pyruvate:ferredoxin oxidoreductase from Giardia duodenalis
    • Townson, S. M.; Upcroft, J. A.; Upcroft, P. Characterisation and purification of pyruvate:ferredoxin oxidoreductase from Giardia duodenalis. Mol. Biochem. Parasitol. 1996, 79, 183-193.
    • (1996) Mol. Biochem. Parasitol , vol.79 , pp. 183-193
    • Townson, S.M.1    Upcroft, J.A.2    Upcroft, P.3
  • 14
    • 0035138734 scopus 로고    scopus 로고
    • Drug targets and mechanisms of resistance in the anaerobic protozoa
    • Upcroft, P.; Upcroft, J. A. Drug targets and mechanisms of resistance in the anaerobic protozoa. Clin. Microbiol. Rev. 2001, 14, 150-164.
    • (2001) Clin. Microbiol. Rev , vol.14 , pp. 150-164
    • Upcroft, P.1    Upcroft, J.A.2
  • 15
    • 0025738916 scopus 로고
    • Concentration of metronidazole in cervical mucus and serum after single and repeated oral doses
    • Salas-Herrera, I. G.; Pearson, R. M.; Johnston, A.; Turner, P. Concentration of metronidazole in cervical mucus and serum after single and repeated oral doses. J. Antimicrob. Chemother. 1991, 28, 283-289.
    • (1991) J. Antimicrob. Chemother , vol.28 , pp. 283-289
    • Salas-Herrera, I.G.1    Pearson, R.M.2    Johnston, A.3    Turner, P.4
  • 16
    • 29944437209 scopus 로고    scopus 로고
    • 5-Nitroimidazole drugs effective against metronidazole-resistant Trichomonas vaginalis and Giardia duodenalis
    • Upcroft, J. A.; Dunn, L. A.; Wright, J. M.; Benakli, K.; Upcroft, P.; et al. 5-Nitroimidazole drugs effective against metronidazole-resistant Trichomonas vaginalis and Giardia duodenalis. Antimicrob. Agents Chemother. 2006, 50, 344-347.
    • (2006) Antimicrob. Agents Chemother , vol.50 , pp. 344-347
    • Upcroft, J.A.1    Dunn, L.A.2    Wright, J.M.3    Benakli, K.4    Upcroft, P.5
  • 17
    • 0032939686 scopus 로고    scopus 로고
    • Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp
    • Upcroft, J. A.; Campbell, R. W.; Benakli, K.; Upcroft, P.; Vanelle, P. Efficacy of new 5-nitroimidazoles against metronidazole-susceptible and -resistant Giardia, Trichomonas, and Entamoeba spp. Antimicrob. Agents Chemother. 1999, 43, 73-76.
    • (1999) Antimicrob. Agents Chemother , vol.43 , pp. 73-76
    • Upcroft, J.A.1    Campbell, R.W.2    Benakli, K.3    Upcroft, P.4    Vanelle, P.5
  • 18
    • 0033102136 scopus 로고    scopus 로고
    • Competition between C- and O-alkylation reactions in 5-nitroimidazole series: Influence of nucleophile
    • Benakli, K.; Kaafarani, M.; Crozet, M. P.; Vanelle, P. Competition between C- and O-alkylation reactions in 5-nitroimidazole series: influence of nucleophile. Heterocycles 1999, 51, 557-565.
    • (1999) Heterocycles , vol.51 , pp. 557-565
    • Benakli, K.1    Kaafarani, M.2    Crozet, M.P.3    Vanelle, P.4
  • 19
    • 0000451948 scopus 로고    scopus 로고
    • Osmium-catalyzed dihydroxylation of olefins in acidic media: Old process, new tricks
    • Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Osmium-catalyzed dihydroxylation of olefins in acidic media: old process, new tricks. Adv. Synth. Catal. 2002, 344, 421-433.
    • (2002) Adv. Synth. Catal , vol.344 , pp. 421-433
    • Dupau, P.1    Epple, R.2    Thomas, A.A.3    Fokin, V.V.4    Sharpless, K.B.5
  • 20
    • 0001346254 scopus 로고
    • Selective reduction of aryl halides and alpha, beta-unsaturated esters with sodium-borohydride cuprous chloride in methanol and its application to deuterium labeling
    • Narisada, M.; Horibe, I.; Watanabe, F.; Takeda, K. Selective reduction of aryl halides and alpha, beta-unsaturated esters with sodium-borohydride cuprous chloride in methanol and its application to deuterium labeling. J. Org. Chem. 1989, 54, 5308-5313.
    • (1989) J. Org. Chem , vol.54 , pp. 5308-5313
    • Narisada, M.1    Horibe, I.2    Watanabe, F.3    Takeda, K.4
  • 21
    • 32344435655 scopus 로고    scopus 로고
    • An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo) benzene
    • Ishihara, M.; Togo, H. An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo) benzene. Synlett 2006, 227-230.
    • (2006) Synlett , pp. 227-230
    • Ishihara, M.1    Togo, H.2
  • 22
    • 27744539009 scopus 로고    scopus 로고
    • Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones. Tools and tactics for solving problems in fluorous mixture synthesis
    • Dandapani, S.; Jeske, M.; Curran, D. P. Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones. Tools and tactics for solving problems in fluorous mixture synthesis. J. Org. Chem. 2005, 70, 9447-9462.
    • (2005) J. Org. Chem , vol.70 , pp. 9447-9462
    • Dandapani, S.1    Jeske, M.2    Curran, D.P.3
  • 23
    • 21244492775 scopus 로고    scopus 로고
    • Preparation and properties of fluorenylidene(phenyl)phosphines bearing bulky groups with electron-donating substituents in the ortho position on the phenyl group
    • Kawasaki, S.; Fujita, T.; Toyota, K.; Yoshifuji, M. Preparation and properties of fluorenylidene(phenyl)phosphines bearing bulky groups with electron-donating substituents in the ortho position on the phenyl group. Bull. Chem. Soc. Jpn. 2005, 78, 1082-1090.
    • (2005) Bull. Chem. Soc. Jpn , vol.78 , pp. 1082-1090
    • Kawasaki, S.1    Fujita, T.2    Toyota, K.3    Yoshifuji, M.4
  • 25
    • 0023836935 scopus 로고
    • Altered uptake of metronidazole in vitro by stocks of Giardia intestinalis with different drug sensitivities
    • Boreham, P. F.; Phillips, R. E.; Shepherd, R. W. Altered uptake of metronidazole in vitro by stocks of Giardia intestinalis with different drug sensitivities. Trans. R. Soc. Trop. Med. Hyg. 1988, 82, 104-106.
    • (1988) Trans. R. Soc. Trop. Med. Hyg , vol.82 , pp. 104-106
    • Boreham, P.F.1    Phillips, R.E.2    Shepherd, R.W.3
  • 26
    • 34447568257 scopus 로고    scopus 로고
    • Clinical implications of multiple drug resistance efflux pumps of pathogenic bacteria
    • Rouveix, B. Clinical implications of multiple drug resistance efflux pumps of pathogenic bacteria. J. Antimicrob. Chemother. 2007, 59, 1208-1209.
    • (2007) J. Antimicrob. Chemother , vol.59 , pp. 1208-1209
    • Rouveix, B.1
  • 27
    • 22144476125 scopus 로고    scopus 로고
    • Bacterial resistance to antibiotics: Enzymatic degradation and modification
    • Wright, G. D. Bacterial resistance to antibiotics: enzymatic degradation and modification. Adv. Drug Delivery Rev. 2005, 57, 1451-1470.
    • (2005) Adv. Drug Delivery Rev , vol.57 , pp. 1451-1470
    • Wright, G.D.1
  • 29
    • 45749123127 scopus 로고    scopus 로고
    • Identification of differentially expressed genes in a Giardia lamblia WB C6 clone resistant to nitazoxanide and metronidazole
    • Muller, J.; Ley, S.; Felger, I.; Hemphill, A.; Muller, N. Identification of differentially expressed genes in a Giardia lamblia WB C6 clone resistant to nitazoxanide and metronidazole. J. Antimicrob. Chemother. 2008, 62, 72-82.
    • (2008) J. Antimicrob. Chemother , vol.62 , pp. 72-82
    • Muller, J.1    Ley, S.2    Felger, I.3    Hemphill, A.4    Muller, N.5
  • 30
    • 33748292892 scopus 로고    scopus 로고
    • Substituent effect on a family of quinones in aprotic solvents: An experimental and theoretical approach
    • Frontana, C.; Vazquez-Mayagoitia, A.; Garza, J.; Vargas, R.; Gonzalez, I. Substituent effect on a family of quinones in aprotic solvents: an experimental and theoretical approach. J. Phys. Chem. A 2006, 110, 9411-9419.
    • (2006) J. Phys. Chem. A , vol.110 , pp. 9411-9419
    • Frontana, C.1    Vazquez-Mayagoitia, A.2    Garza, J.3    Vargas, R.4    Gonzalez, I.5
  • 31
    • 0032933759 scopus 로고    scopus 로고
    • An experimental and theoretical study of the substituent effects on the redox properties of 2-[(R-phenyl) amine]-1,4-naphthalenediones in acetonitrile
    • Aguilar-Martinez, M.; Cuevas, G.; Jimenez-Estrada, M.; Gonzalez, I.; Lotina-Hennsen, B.; et al. An experimental and theoretical study of the substituent effects on the redox properties of 2-[(R-phenyl) amine]-1,4-naphthalenediones in acetonitrile. J. Org. Chem. 1999, 64, 3684-3694.
    • (1999) J. Org. Chem , vol.64 , pp. 3684-3694
    • Aguilar-Martinez, M.1    Cuevas, G.2    Jimenez-Estrada, M.3    Gonzalez, I.4    Lotina-Hennsen, B.5
  • 32
    • 0037131357 scopus 로고    scopus 로고
    • Tuning the redox chemistry of 4-benzoyl-N-methylpyridinium cations through para substitution. Hammett linear free energy relationships and the relative aptitude of the two-electron reduced forms for H-bonding
    • Leventis, N.; Rawaswdeh, A. M. M.; Zhang, G. H.; Elder, I. A.; Sotiriou-Leventis, C. Tuning the redox chemistry of 4-benzoyl-N-methylpyridinium cations through para substitution. Hammett linear free energy relationships and the relative aptitude of the two-electron reduced forms for H-bonding. J. Org. Chem. 2002, 67, 7501-7510.
    • (2002) J. Org. Chem , vol.67 , pp. 7501-7510
    • Leventis, N.1    Rawaswdeh, A.M.M.2    Zhang, G.H.3    Elder, I.A.4    Sotiriou-Leventis, C.5
  • 33
    • 0346364993 scopus 로고    scopus 로고
    • Model systems for flavoenzyme activity: Relationships between cofactor structure, binding and redox properties
    • Legrand, Y. M.; Gray, M.; Cooke, G.; Rotello, V. M. Model systems for flavoenzyme activity: relationships between cofactor structure, binding and redox properties. J. Am. Chem. Soc. 2003, 125, 15789-15795.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 15789-15795
    • Legrand, Y.M.1    Gray, M.2    Cooke, G.3    Rotello, V.M.4
  • 34
    • 0042440143 scopus 로고
    • An extended table of Hammett substituent constants based on the ionization of substituted benzoic acids
    • Mcdaniel, D. H.; Brown, H. C. An extended table of Hammett substituent constants based on the ionization of substituted benzoic acids. J. Org. Chem. 1958, 23, 420-427.
    • (1958) J. Org. Chem , vol.23 , pp. 420-427
    • Mcdaniel, D.H.1    Brown, H.C.2
  • 35
    • 0033272113 scopus 로고    scopus 로고
    • Voltammetric behaviour of metronidazole at mercury electrodes
    • La-Scalea, M. A.; Serrano, S. H. P.; Gutz, I. G. R. Voltammetric behaviour of metronidazole at mercury electrodes. J. Braz. Chem. Soc. 1999, 10, 127-135.
    • (1999) J. Braz. Chem. Soc , vol.10 , pp. 127-135
    • La-Scalea, M.A.1    Serrano, S.H.P.2    Gutz, I.G.R.3
  • 36
    • 0036310976 scopus 로고    scopus 로고
    • Methods for cultivation of luminal parasitic protists of clinical importance
    • Clark, C. G.; Diamond, L. S. Methods for cultivation of luminal parasitic protists of clinical importance. Clin. Microbiol. Rev. 2002, 15, 329-341.
    • (2002) Clin. Microbiol. Rev , vol.15 , pp. 329-341
    • Clark, C.G.1    Diamond, L.S.2


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