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Volumn 48, Issue 17, 2005, Pages 5480-5488

Synthesis, DNA affinity, and antiprotozoal activity of fused ring dicationic compounds and their prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

2,7 BIS(N' ETHOXYCARBONYL N'' ISOPROPYL)GUANIDINO 9H FLUORENE; 2,7 BIS(N' ETHOXYCARBONYL)GUANIDINO 9H FLUORENE; 2,7 BIS(N' ETHOXYCARBONYL)GUANIDINOFLUOREN 9 ONE; 2,7 BIS(N' ETHYL)GUANIDINO 9H FLUORENE; 2,7 BIS(N' ISOPROPYL)GUANIDINO 9H FLUORENE; 2,7 BIS(N' METHYL)GUANIDINO 9H FLUORENE; 2,7 BIS[4 (IMINOBENZYLAMINO)] 9H FLUORENE; 2,7 BIS[4 [IMINO (2 PYRIDYLMETHYL)]AMINO] 9H FLUORENE; 2,7 BISGUANIDINO 9H FLUORENE; 2,7 BISGUANIDINOANTHRAQUINONE; 2,7 BISGUANIDINOFLUOREN 9 ONE; 2,7 NIS(N ETHOXYCARBONYL N'' METHYL)GUANIDINO 9H FLUORENE; 3,6 BISGUANIDINOACRIDINE; AMIDINE; GUANIDINE DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

EID: 23944453324     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm058190h     Document Type: Article
Times cited : (67)

References (48)
  • 1
    • 0038268392 scopus 로고    scopus 로고
    • Dicationic DNA minor groove binders as antimicrobial agents
    • Demeunynck, M., Bailly, C., Wilson, W. D., Eds.; Wiley-VCH: Weinheim, Germany
    • (a)Tidwell, R. R.; Boykin, W. D. Dicationic DNA Minor Groove Binders as Antimicrobial Agents. In Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes, Demeunynck, M., Bailly, C., Wilson, W. D., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 2, pp 416-460.
    • (2002) Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes , vol.2 , pp. 416-460
    • Tidwell, R.R.1    Boykin, W.D.2
  • 2
    • 22144474782 scopus 로고    scopus 로고
    • Dications that target the DNA minor groove: Compound design and preparation, DNA interactions, cellular distribution and biological activity
    • (b) Wilson, W. D.; Nguyen, B.; Tanious, F. A.; Mathis, A.; Hall, J. E.; Stephens, C. E.; Boykin, D. W. Dications That Target the DNA Minor Groove: Compound Design and Preparation, DNA Interactions, Cellular Distribution and Biological Activity. Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 389-408.
    • (2005) Curr. Med. Chem. Anti-Cancer Agents , vol.5 , pp. 389-408
    • Wilson, W.D.1    Nguyen, B.2    Tanious, F.A.3    Mathis, A.4    Hall, J.E.5    Stephens, C.E.6    Boykin, D.W.7
  • 3
    • 37049147845 scopus 로고
    • Chemotherapeutic comparison of the trypanocidal action of some aromatic diamidines
    • Ashley, J. N.; Barber, H. J.; Ewins, A. J.; Newbery, G.; Self, A. D. H. Chemotherapeutic Comparison of the Trypanocidal Action of Some Aromatic Diamidines. J. Chem. Soc. 1942, 103-106.
    • (1942) J. Chem. Soc. , pp. 103-106
    • Ashley, J.N.1    Barber, H.J.2    Ewins, A.J.3    Newbery, G.4    Self, A.D.H.5
  • 4
    • 0142258170 scopus 로고    scopus 로고
    • Chemotherapy of human African trypanosomiasis: Current and future prospects
    • Fairlamb, A. H. Chemotherapy of Human African Trypanosomiasis: Current and Future Prospects. Trends Parasitol. 2003, 19, 488-494.
    • (2003) Trends Parasitol. , vol.19 , pp. 488-494
    • Fairlamb, A.H.1
  • 8
    • 0028025544 scopus 로고
    • Selective inhibition of Topoisomerases from Pneumocystis carinii compared with that of topoisomerases from mammalian cell
    • Dykstra, C. C.; McClernon, D. R.; Elwell, L. P.; Tidwell, R. R. Selective Inhibition of Topoisomerases from Pneumocystis carinii Compared with That of Topoisomerases from Mammalian Cell. Antimicrob. Agents Chemother. 1994, 38, 1890-1898.
    • (1994) Antimicrob. Agents Chemother. , vol.38 , pp. 1890-1898
    • Dykstra, C.C.1    McClernon, D.R.2    Elwell, L.P.3    Tidwell, R.R.4
  • 9
    • 0032913039 scopus 로고    scopus 로고
    • Relationships between topoisomerase II inhibition, sequence-specificity and DNA binding mode of dicationic diphenylftiran derivatives
    • Bailly, C.; Dassonneville, L.; Carrascol, C.; Lucasl, D.; Kumar, A.; Boykin, D. W.; Wilson. W. D. Relationships between Topoisomerase II Inhibition, Sequence-Specificity and DNA Binding Mode of Dicationic Diphenylftiran Derivatives. Anti-Cancer Drug Des. 1999, 14, 47-60.
    • (1999) Anti-Cancer Drug Des. , vol.14 , pp. 47-60
    • Bailly, C.1    Dassonneville, L.2    Carrascol, C.3    Lucasl, D.4    Kumar, A.5    Boykin, D.W.6    Wilson, W.D.7
  • 10
    • 0033578872 scopus 로고    scopus 로고
    • Selective nucleosome disruption by drugs that bind in the minor groove of DNA
    • Fitzgerald, D. J.; Anderson, J. N. Selective Nucleosome Disruption by Drugs That Bind in the Minor Groove of DNA. J. Biol. Chem. 1999, 274, 27128-27138.
    • (1999) J. Biol. Chem. , vol.274 , pp. 27128-27138
    • Fitzgerald, D.J.1    Anderson, J.N.2
  • 11
    • 0029028144 scopus 로고
    • Molecular struggle for transcription control
    • Henderson, D.; Hurley, L. H. Molecular Struggle for Transcription Control. Nat. Med. 1995, 1, 525-527.
    • (1995) Nat. Med. , vol.1 , pp. 525-527
    • Henderson, D.1    Hurley, L.H.2
  • 12
    • 0022900621 scopus 로고
    • Isohelical analysis of DNA groove-binding drugs
    • Goodsell, D.; Dickerson, R. E. Isohelical Analysis of DNA Groove-Binding Drugs. J. Med. Chem. 1986, 29, 727-733.
    • (1986) J. Med. Chem. , vol.29 , pp. 727-733
    • Goodsell, D.1    Dickerson, R.E.2
  • 13
    • 0026578006 scopus 로고
    • Structure and DNA binding activity of analogues of 1,5-Bis(4- amidinophenoxy)-pentane (Pentamidine)
    • Cory, M.; Tidwell, R. R.; Fairley, T. A. Structure and DNA Binding Activity of Analogues of 1,5-Bis(4-amidinophenoxy)-pentane (Pentamidine). J. Med. Chem. 1992, 35, 431-438.
    • (1992) J. Med. Chem. , vol.35 , pp. 431-438
    • Cory, M.1    Tidwell, R.R.2    Fairley, T.A.3
  • 15
    • 0037145991 scopus 로고    scopus 로고
    • Strong binding in the DNA minor groove by an aromatic diamidine with a shape that does not match the curvature of the groove
    • Nguyen, B.; Lee, M. P. H.; Hamelberg, D.; Joubert, A.; Bailly, C.; Brun, R.; Neidle, S.; Wilson, D. W. Strong Binding in the DNA Minor Groove by an Aromatic Diamidine with a Shape That Does Not Match the Curvature of the Groove. J. Am. Chem. Soc. 2002, 124, 13680-13681.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13680-13681
    • Nguyen, B.1    Lee, M.P.H.2    Hamelberg, D.3    Joubert, A.4    Bailly, C.5    Brun, R.6    Neidle, S.7    Wilson, D.W.8
  • 18
    • 0032728386 scopus 로고    scopus 로고
    • Dicationic dibenzofuran derivatives as anti-pneumocystis carinii pneumonia agents: Synthesis, DNA binding affinity, and anti-PCP activity
    • Wang, S. H.; Hall, J. E.; Tanious, F. A.; Wilson, W. D.; Patrick, D. A.; McCurdy, D. R.; Bender, B. C.; Tidwell, R. R. Dicationic Dibenzofuran Derivatives as Anti-Pneumocystis Carinii Pneumonia Agents: Synthesis, DNA Binding Affinity, and Anti-PCP Activity. Eur. J. Med. Chem. 1999, 34, 215-224.
    • (1999) Eur. J. Med. Chem. , vol.34 , pp. 215-224
    • Wang, S.H.1    Hall, J.E.2    Tanious, F.A.3    Wilson, W.D.4    Patrick, D.A.5    McCurdy, D.R.6    Bender, B.C.7    Tidwell, R.R.8
  • 19
    • 0032710064 scopus 로고    scopus 로고
    • Synthesis and anti-Pneumocystis carinii pneumonia activity of novel dicationic dibenzothiophenes and orally active prodrugs
    • Patrick, D. A.; Hall, J. E.; Bender, B. C.; McCurdy, D. R.; Wilson, W. D.; Tanious, F. A.; Saha, S.; Tidwell, R. R. Synthesis and Anti-Pneumocystis carinii Pneumonia Activity of Novel Dicationic Dibenzothiophenes and Orally Active Prodrugs. Eur. J. Med. Chem. 1999, 34, 575-583.
    • (1999) Eur. J. Med. Chem. , vol.34 , pp. 575-583
    • Patrick, D.A.1    Hall, J.E.2    Bender, B.C.3    McCurdy, D.R.4    Wilson, W.D.5    Tanious, F.A.6    Saha, S.7    Tidwell, R.R.8
  • 20
    • 0030668024 scopus 로고    scopus 로고
    • A new type of DNA minor-groove complex: Carbazole dication-DNA interactions
    • Tanious, F. A.; Ding, D.; Patrick, D. A.; Tidwell, R. R.; Wilson, W. D. A New Type of DNA Minor-Groove Complex: Carbazole Dication-DNA Interactions. Biochemistry 1997, 36, 15315-15325.
    • (1997) Biochemistry , vol.36 , pp. 15315-15325
    • Tanious, F.A.1    Ding, D.2    Patrick, D.A.3    Tidwell, R.R.4    Wilson, W.D.5
  • 21
    • 0034601825 scopus 로고    scopus 로고
    • Effects of compound structure on carbazole dication-DNA complexes: Tests of the minor-groove complex models
    • Tanious, F. A.; Ding, D.; Patrick, D. A.; Bailly, C.; Tidwell, R. R.; Wilson, W. D. Effects of Compound Structure on Carbazole Dication-DNA Complexes: Tests of the Minor-Groove Complex Models. Biochemistry 2000, 39, 12091-12101.
    • (2000) Biochemistry , vol.39 , pp. 12091-12101
    • Tanious, F.A.1    Ding, D.2    Patrick, D.A.3    Bailly, C.4    Tidwell, R.R.5    Wilson, W.D.6
  • 23
    • 0037763899 scopus 로고    scopus 로고
    • The activity of diguanidino and "reversed" diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani
    • Stephens, C. E.; Brun, R.; Salem, M. M.; Werbovetz, K. A.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. The Activity of Diguanidino and "Reversed" Diamidino 2,5-Diarylfurans versus Trypanosoma cruzi and Leishmania donovani. Bioorg. Med. Chem. Lett. 2003, 13, 2065-2069.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2065-2069
    • Stephens, C.E.1    Brun, R.2    Salem, M.M.3    Werbovetz, K.A.4    Tanious, F.A.5    Wilson, W.D.6    Boykin, D.W.7
  • 24
    • 1842779964 scopus 로고    scopus 로고
    • Bisguanidine, Bi(2-aminoimidazoline), and polyamine Dervatives as potent and selective chemotherapeutic agents against Trypanosoma brucei rhodensiense. Synthesis and in vitro evauation
    • Dardonville, C.; Brun, R. Bisguanidine, Bi(2-aminoimidazoline), and Polyamine Dervatives as Potent and Selective Chemotherapeutic Agents against Trypanosoma brucei rhodensiense. Synthesis and in Vitro Evauation. J. Med. Chem. 2004, 47, 2296-2307.
    • (2004) J. Med. Chem. , vol.47 , pp. 2296-2307
    • Dardonville, C.1    Brun, R.2
  • 25
    • 0001308280 scopus 로고
    • Patai, S., Ed.; John Wiley & Sons: Chichester, U.K.
    • Oszczapowicz, J. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1991; Vol. 2, pp 623-688.
    • (1991) The Chemistry of Amidines and Imidates , vol.2 , pp. 623-688
    • Oszczapowicz, J.1
  • 27
    • 2342481809 scopus 로고    scopus 로고
    • Lessons learned from marketed and investigational prodrugs
    • Ettmayer, P.; Amidon, G. L.; Clement, B.; Testa, B. Lessons Learned from Marketed and Investigational Prodrugs. J. Med. Chem. 2004, 47, 2392-2404.
    • (2004) J. Med. Chem. , vol.47 , pp. 2392-2404
    • Ettmayer, P.1    Amidon, G.L.2    Clement, B.3    Testa, B.4
  • 28
    • 0036038490 scopus 로고    scopus 로고
    • Reduction of N-hydroxylated compounds: Amidioximes (N-Hydroxyamidines) as prodrugs of amidines
    • Clement, B. Reduction of N-Hydroxylated Compounds: Amidioximes (N-Hydroxyamidines) as Prodrugs of Amidines. Drug Metab. Rev. 2002, 34, 565-579.
    • (2002) Drug Metab. Rev. , vol.34 , pp. 565-579
    • Clement, B.1
  • 29
    • 3843134198 scopus 로고    scopus 로고
    • O-Alkoxyamidine prodrugs of furamidine: In vitro transport and microsomal metabolism as indicators of in vivo efficacy in a mouse model of Trypanosoma brucei rhodesiense infection
    • Ansede, J.; Anbazhagan, M.; Brun, R.; Easterbrook, J.; Hall, J. E.; Boykin, D. W. O-Alkoxyamidine Prodrugs of Furamidine: In Vitro Transport and Microsomal Metabolism as Indicators of in Vivo Efficacy in a Mouse Model of Trypanosoma brucei rhodesiense Infection. J. Med. Chem. 2004, 47, 4335-4338.
    • (2004) J. Med. Chem. , vol.47 , pp. 4335-4338
    • Ansede, J.1    Anbazhagan, M.2    Brun, R.3    Easterbrook, J.4    Hall, J.E.5    Boykin, D.W.6
  • 30
    • 0030591850 scopus 로고    scopus 로고
    • Anti-pneumocystis activity of Bis-amidoximes and Bis-O-alkylamidoximes prodrugs
    • Boykin, D. W.; Kumar, A.; Bender, B. C.; Hall, J. E.; Tidwell, R. R. Anti-Pneumocystis Activity of Bis-amidoximes and Bis-O-alkylamidoximes Prodrugs. Bioorg. Med. Chem. Lett. 1996, 6, 3017-3020.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 3017-3020
    • Boykin, D.W.1    Kumar, A.2    Bender, B.C.3    Hall, J.E.4    Tidwell, R.R.5
  • 33
    • 0033598329 scopus 로고    scopus 로고
    • Prodrugs for amidines: Synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-Bis-[4-amidinophenyl]furan
    • Rahmathullah, S. M.; Hall, J. E.; Brender, B. C.; McCurdy, D. R.; Tidwell, R. R.; Boykin, D. W. Prodrugs for Amidines: Synthesis and Anti-Pneumocystis carinii Activity of Carbamates of 2,5-Bis-[4-amidinophenyl] furan. J. Med. Chem. 1999, 42, 3994-4000.
    • (1999) J. Med. Chem. , vol.42 , pp. 3994-4000
    • Rahmathullah, S.M.1    Hall, J.E.2    Brender, B.C.3    McCurdy, D.R.4    Tidwell, R.R.5    Boykin, D.W.6
  • 36
    • 12244298917 scopus 로고    scopus 로고
    • Oxidative activation of acylguanidine prodrugs: Intestinal presystemic activation in rats limits absortion and can be inhibited by Co-administration of ketoconazole
    • Humphreys, W. G.; Obermeier, M. T.; Chong, S.; Kimball, S. D.; Das, J.; Chen, P.; Moquin, R.; Han, W.-H.; Gedamke, R.; White, R. E.; Morrison, R. A. Oxidative Activation of Acylguanidine Prodrugs: Intestinal Presystemic Activation in Rats Limits Absortion and Can Be Inhibited by Co-administration of Ketoconazole. Xenobiotica 2003, 33, 93-106.
    • (2003) Xenobiotica , vol.33 , pp. 93-106
    • Humphreys, W.G.1    Obermeier, M.T.2    Chong, S.3    Kimball, S.D.4    Das, J.5    Chen, P.6    Moquin, R.7    Han, W.-H.8    Gedamke, R.9    White, R.E.10    Morrison, R.A.11
  • 37
  • 39
    • 0027371231 scopus 로고
    • Improved method for the preparation of guanidines
    • Kim, K. S.; Qian, L. Improved Method for the Preparation of Guanidines. Tetrahedron Lett. 1993, 34, 7677-7680.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7677-7680
    • Kim, K.S.1    Qian, L.2
  • 40
    • 0030936351 scopus 로고    scopus 로고
    • 2-promoted guanylation reaction: The scope and limitations
    • 2-Promoted Guanylation Reaction: The Scope and Limitations. Tetrahedron 1997, 53, 5291-5304.
    • (1997) Tetrahedron , vol.53 , pp. 5291-5304
    • Levallet, C.1    Lerpiniere, J.2    Ko, S.Y.3
  • 41
    • 0032546306 scopus 로고    scopus 로고
    • Conversion of N,N′-Bis(tert-butoxycarbonyl)-guanidines to N-N′-tert-Butoxycarbonylamidinoureas
    • Miel, H.; Rault, S. Conversion of N,N′-Bis(tert-butoxycarbonyl)- guanidines to N-N′-tert-Butoxycarbonylamidino)ureas. Tetrahedron Lett. 1998, 39, 1565-1568.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1565-1568
    • Miel, H.1    Rault, S.2
  • 42
    • 0024853020 scopus 로고
    • A facile synthesis of cyanoguanidines from thioureas
    • Atwal, K. S.; Ahmed, S. Z.; O'Reilly, B. C. A Facile Synthesis of Cyanoguanidines from Thioureas. Tetrahedron Lett. 1989, 30, 7313-7316.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7313-7316
    • Atwal, K.S.1    Ahmed, S.Z.2    O'Reilly, B.C.3
  • 43
    • 0029003207 scopus 로고
    • Cardioselective antiischemic ATP-sensitive potassium channel openers. 2. Structure activity studies on benzopyranylcyanoguanidines: Modification of the benzopyran ring
    • Atwal, K. S.; Grover, G. J.; Ferrara, F. N.; Ahmed, S. Z.; Sleph, P. G.; Dzwonczyk, S.; Normandin, D. E. Cardioselective Antiischemic ATP-Sensitive Potassium Channel Openers. 2. Structure Activity Studies on Benzopyranylcyanoguanidines: Modification of the Benzopyran Ring. J. Med. Chem. 1995, 38, 1966-1973.
    • (1995) J. Med. Chem. , vol.38 , pp. 1966-1973
    • Atwal, K.S.1    Grover, G.J.2    Ferrara, F.N.3    Ahmed, S.Z.4    Sleph, P.G.5    Dzwonczyk, S.6    Normandin, D.E.7
  • 44
    • 0034629104 scopus 로고    scopus 로고
    • A versatile one-pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates
    • Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. A Versatile One-Pot Synthesis of 1,3-Substituted Guanidines from Carbamoyl Isothiocyanates. J. Org. Chem. 2000, 65, 1566-1568.
    • (2000) J. Org. Chem. , vol.65 , pp. 1566-1568
    • Linton, B.R.1    Carr, A.J.2    Orner, B.P.3    Hamilton, A.D.4
  • 46
    • 33645476404 scopus 로고    scopus 로고
    • note
    • Three rotational isomers are possible: syn-syn, syn-anti, and anti-anti. However, we see only two sets of NMR signals.
  • 48
    • 0031021264 scopus 로고    scopus 로고
    • S-2-Naphthylmethyl thioacetimidate hydrobromide: A new odorless reagent for the mild synthesis of substituted acetamidines
    • Shearer, B. G.; Oplinger, J. A.; Lee, S. S-2-Naphthylmethyl Thioacetimidate Hydrobromide: A New Odorless Reagent for the Mild Synthesis of Substituted Acetamidines. Tetrahedron Lett. 1997, 38, 179-182.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 179-182
    • Shearer, B.G.1    Oplinger, J.A.2    Lee, S.3


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