Extended aromatic furan amidino derivatives as anti-Pneumocystis carinii agents

Journal of Medicinal Chemistry

Volumn 41, Issue 20, 1998, Pages 3872-3878

  Hopkins, Katherine T ^a   Wilson, W David ^a   Bender, Brendan C ^b   McCurdy, Donald R ^b   Hall, James Edwin ^b,c   Tidwell, Richard R ^b   Kumar, Arvind ^a   Bajic, Miro ^a   Boykin, David W ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c IL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPROTOZOAL AGENT; FURAN DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG DNA BINDING; DRUG SYNTHESIS; NONHUMAN; PNEUMOCYSTIS CARINII; PNEUMOCYSTOSIS; RAT;

AMIDINES; ANIMALS; ANTIFUNGAL AGENTS; DRUG EVALUATION, PRECLINICAL; FURANS; IMMUNOSUPPRESSION; OLIGODEOXYRIBONUCLEOTIDES; PNEUMONIA, PNEUMOCYSTIS; POLY DA-DT; PROTEIN BINDING; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032563982     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980230c     Document Type: Article

References (31)

1. Boykin, D. W.; Kumar, A.; Spychala, J.; Zhou, M.; Lombardy, R. J.; Wilson, W. D.; Dykstra, C. C.; Jones, S. K.; Hall, J. E.; Tidwell, R. R.; Loughton, C.; Nunn, C. M.; Neidle, S. Dicationic Diarylfurans as Anti-Pneumocystis carinii Agents. J. Med. Chem. 1995, 38, 912-916.
2. Tidwell, R. R.; Jones, S. K.; Naiman, N. A.; Berger, L. C.; Brake, W. B.; Dykstra, C. C.; Hall, J. E. Activity of Cationically Substituted Bis-benzimidazoles against Experimental Pneumocystis carinii pneumonia. Antimicrob. Agents Chemother. 1993, 37, 1713-1716.
3. Lombardy, R. L.; Tarderas, F. A.; Ramachandran, K.; Tidwell, R. R.; Wilson, W. D. Synthesis and DNA Interactions of Benzimidazole Dications which have Activity against Opportunistic Infections. J. Med. Chem. 1996, 39, 1452-1462.
4. Bell, C. A.; Dykstra, C. C.; Naiman, N. N.; Cory, M.; Fairley, T. A.; Tidwell, R. R. Structure-activity studies of dicationic substituted bis-benzimidazoles against Giardia lamblia: Correlation of antigiardial activity with DNA binding affinity and giardial topoisomerase II inhibition. Antimicrob. Agents Chemother. 1993, 37, 2668-2673.
5. Blagburn, B. L.; Sundermann, C. A.; Lindsay, D. S.; Hall, J. E.; Tidwell, R. R. Inhibition of Crytosporidium parvum in neonatal Hsd:(1CR)BR swiss miceby polyether ionophores and aromatic amidines. Antimicrob. Agents Chemother. 1991, 35, 1520-1523.
6. Boykin, D. W.; Kumar, A.; Xiao, G.; Wilson, W. D.; Bender, B. C.; McCurdy, D. R.; Hall, J. E.; Tidwell, R. R. 2,5-Bis[4(N-alkylamidino)phenyl]furans as Anti-Pneumocystis carinii Agents. J. Med. Chem. 1998, 41, 124-129.
7. Tidwell, R. R.; Bell, C. A. Pentamidine and Related Compounds in Treatment of Pneumocystis carinii Infection. Pneumocystis carinii; Marcel Decker: New York, 1993; pp 561-583.
8. Henderson, D.; Hurley, L. H. Molecular Struggle for Transcription Control. Nature Med. 1995, 1, 525-527.
9. Beerman, T. A.; McHugh, M. M.; Sigmund, R.; Lown, J. W.; Rao, K. E.; Bathim, Y. Effects of Analogues of the DNA Minor Groove Binder Hoechst 33258 on Topoisomerase I and II Mediated Activity. Biochim. Biophys. Acta 1992, 1131, 52-61.
10. Bell, C. A.; Cory, M.; Fairley, T. A.; Hall, J. E.; Tidwell, R. R. Structure-Activity Relationships of Pentamidine Analogues against Giardia lamblia: Correlation of antigiardial activity with DNA binding affinity and giardial topoisomerase II inhibition. Antimicrob. Agents Chemother. 1991, 35, 1099-1107.
11. 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 Cells. Antimicrob. Agents Chemother. 1994, 38, 1890-1898.
12. Hildebrandt, E.; Boykin, D. W.; Kumar, A.; Tidwell, R. R.; Dykstra, C. C. Identification and Characterization of an Endo/ Exonuclease in Pneumocystis carinii that is Inhibited by Dicationic Diarylfurans with Efficacy Against Pneumocystis pneumonia. Implications for Mechanism of Antimicrobial Action. J. Euk. Microbiol. 1998, 45, 112-121.
13. Das, B. P.; Boykin, D. W. Synthesis and Antiprotozoal Activity of2,5-bis(4-guanylphenyl)furans. J. Med. Chem. 1977, 20, 531-536.
14. Steck, E. A.; Kinnamon, K. K.; Davidson, D. E.; Duxbury, R. E.; Johnson, A. J.; Masters, R. E. Trypanosoma rhodesiense: Evaluation of the Antitrypanosomal Action of 2,5-bis(4-Guanylphenyl)-furan Dihydrochloride. Exp. Parasitol. 1982, 53, 133-144.
15. Tanious, F. A.; Spychala, J.; Kumar, A.; Greene, K.; Boykin, D. W.; Wilson, W. D. Different binding mode in AT and GC sequences for unfused-aromatic dications. J. Biomol. Struct. Dyn. 1994, 11, 1063-1083.
16. Wilson, W. D.; Tanious, F. A.; Buczak, H.; Venkatramanan, M. K.; Das, B. P.; Boykin, D. W. The Effects of Ligand Struture on Binding Mode and Specificity in the Interaction of Unfused Aromatic Cations. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions; Pullman J., Ed.; Kluwer Academic Publishers: The Netherlands, 1990; pp 331-353.
17. Pilch, D. S.; Kirolos, M. A.; Lui, X.; Plum, G. E.; Breslauer, K. J. Berenil [1,3-Bis(4′-amidinophenylHriazene Binding to DNA Duplexes and to a RNA Duplex: Evidence for Both Intercalative and Mnior Groove Binding Properties. Biochemistry 1995, 34, 9962-9976.
18. Wilson, W. D.; Tanious, F. A.; Barton, H.; Jones, R. L.; Strekowski, L.; Boykin, D. W. Binding of 4′,6-diamidino-2 phenylindole (DAPI) to GC sequences in DNA. J. Am. Chem. Soc. 1989, 11, 5008-5010.
19. Coury, J. E.; McFail-Isom, L.; Williams, L. D.; Bottomley, L. A. A Novel Assay for Drug-DNA Binding Mode, Affinity, and Exclusion Number: Scanning Force Microscopy. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12283-12286.
20. Jansen, K.; Lincoln, P.; Norden, B. Binding of a DAPI analogue 2,5-bis(4-amidinophenyl)furan to DNA. Biochemistry 1993, 32, 6605-6612.
21. Czarny, A.; Boykin, D. W.; Wood, A. A.; Nunn, C. M.; Neidle, S.; Zhao, M.; Wilson, W. D. Analysis of van der Waals and Electrostatic Contributions in the Interactions of Minor Groove Binding Benzimidazoles with DNA. J. Am. Chem. Soc. 1995, 117, 4716-4717.
22. Cory, M.; Tidwell, R. R.; Fairley, T. Structure and DNA Binding Activity of Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine). J. Med. Chem. 1992, 35, 431-438.
23. 2. J. Med. Chem. 1996, 39, 4554-4562.
24. Wilson, W. D.; Ratmeyer, L.; Zhao, M.; Strekowski, L.; Boykin, D. W. The Search for Structure-Specific Nucleic Acid-Interactive Drugs: Effects of Compound Structure on RNA Versus DNA Interaction Strength. Biochemistry 1993, 32, 4098-4104.
25. Wilson, W. D.; Tanious, F. A.; Fernandez-Saiz, M.; Rigl, C. T. Evaluation of Drug-Nucleic Acid Interactions by Thermal Melting Curves. In Drug DNA Protocols; Fox, K. R., Ed.; Humana Press: Totowa, NJ, 1996.
26. Firouzabadi, H. Ghadheri Barium Manganate. An Efficient Oxidizing Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds. Tetrahedron Lett. 1978, 839-840.
27. Tidwell, R. R.; Geratz, J. D.; Dann, O.; Volz, G.; Zeh, D.; Loewe, H. Diarylamidine Derivatives With One or Both of the Aryl Moieties Consisting of an Indole or Indole-like Ring. J. Med. Chem. 1978, 21, 613-623.
28. Kumar, S.; Kansal, V.; Bhaduri, A. Possible Anthelmintic Agents: Syntheses of Ethyl 5(6)-[5(6)-substituted-2-benzimidazolyl)benzimidazole-2-carbamates and Ethyl 4,6-dinitro-5-substituted-aminobenzimidazole-2-carbamates. Indian J. Chem. 1981, 20B, 254-256.
29. Kovac, J.; Krutosikova, A.; Frimm, R. Preperation of Substituted 5-phenyl-2-furfuryl bromides, isocyanates, and thiocyanates. Chem. Zvesti. 1973, 27, 107-111.
30. Krutosikova, A.; Kovac, J.; Sykora, V. The Synthesis of 5-aryl-2-furancarboxylic acids. Collect. Czech. Chem. Commun. 1974, 39, 1892-1897.
31. Spychala, J.; Boykin, D. W.; Wilson, W. D.; Zhao, M.; Tidwell, R. R.; Dykstra, C. C.; Hall, J. E.; Jones, S. K.; Schinazi, R. F. Synthesis of Dicationic Diaryltriazines Nucleic Acid Binding Agents. Eur. J. Med. Chem. 1994, 29, 363-367.