Synthesis, biological activity, and QSAR studies of antimicrobial agents containing biguanide isosteres

Australian Journal of Chemistry

Volumn 57, Issue 1, 2004, Pages 77-85

  Wernert, Gregory T ^a   Winkler, David A ^a   Holan, George ^b   Nicoletti, Gina ^c  

^a CSIRO   (Australia)

^b BAKER IDI HEART AND DIABETES INSTITUTE   (Australia)

^c RMIT UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; BACTERIA; CONFORMATIONS; MOLECULES; PHOSPHOLIPIDS; SYNTHESIS (CHEMICAL);

ANTIMICROBIAL ACTIVITY; ANTIMICROBIAL AGENTS; ANTIMICROBIAL EFFECT; BIGUANIDE ISOSTERES; CHLORHEXIDINE; LIPOPHILICITY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

AGENTS;

EID: 1142268957     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH03146     Document Type: Article

References (46)

1. Pesticide Manual, 10th Edition (Ed. C. Tomlin) 1994 (Royal Society of Chemistry: London).
2. (a) G. E. Davies, J. Francis, A. R. Martin, F. L. Rose, G. Swain, Br. J. Pharmacol. 1954, 9, 192.
3. (b) F. L. Rose, G. Swain, J. Chem. Soc. 1956, 4422.
4. R. E. Johnson, A. E. Soria, J. R. O'Connor, R. A. Dobson, J. Med. Chem. 1981, 24, 1314.
5. D. M. Bailey, C. G. De Grazia, S. J. Hoff, P. L. Schulenberg, J. R. O'Connor, D. A. Paris, A. McKenzie Slee, J. Med. Chem. 1984, 27, 1457.
6. M. L. Arnold, A. D. Duriatti, M. Jung, R. B. Katz, J. W. Liebeschuetz, Pestic. Sci. 1995, 44, 341.
7. M. A. Ghannoum, N. M. Moussa, P. Whittaker, I. Swairjo, K. H. Abu-Elteen, Chemother. 1992, 38, 46.
8. F. C. Sheppard, D. J. Mason, S. F. Bloomfield, V. A. Gant, FEMS Microbiol. Lett. 1997, 154, 283. doi: 10.1016/SO378-1097(97)00343-1
9. S. P. Denyer, Int. Biodeterior. Biodegrad. 1995, 36, 227. doi: 10.1016/0964-8305(96)00015-7
10. S. P. Denyer, G. S. A. B. Stewart, Int. Biodeterior. Biodegrad. 1998, 41, 261. doi: 10.1016/S0964-8305(98)00023-7
11. T. E. Gunda, A. M. P. Koskinen, Eur. J. Med. Chem. 1991, 26, 449.
12. V. D. Warner, D. M. Lynch, K. H. Kim, G. L. Grunewald, J. Med. Chem. 1979, 22, 359.
13. S. Lindholm, Ann. Acad. Sci. Fenn., Ser. A2: Chem. 1990, 231, 1.
14. D. A. Winkler, G. Holan, in Rational Approaches to Structure, Activity and Ecotoxicology of Agrochemicals (Eds. T. Fujita, W. Draber) 1992, p. 123 (CRC Press: Boca Raton, FL).
15. F. R. Burden, B. Rosewarne, D. A. Winkler, Chemome. Intell. Lab. Syst. 1997, 38, 127. doi: 10.1016/S0169-7439(97)00052-X
16. D. A. Winkler, Briefings Bioinform. 2002, 3, 73.
17. Y. Murata, E. Miyamoto, M. Ueda, J. Pharm. Sci. 1991, 80, 26.
18. R. A. Coburn, M. T. Clark, R. T. Evans, R. J. Genco, J. Med. Chem. 1987, 30, 205.
19. J. Anné, E. De Clercq, H. Eyssen, O. Dann, Antimicrob. Agents Chemother. 1980, 18, 231.
20. L. Fabbrizzi, M. Chicheloni, P. Paoletti, G. Schwarzenbach, J. Am. Chem. Soc. 1977, 99, 5574.
21. A. A. Pinkerton, D. Schwarzenbach, J. Chem. Soc., Dalton Trans. 1978, 8, 989.
22. M. J. Jordan, J. E. Gready, J. Comput. Chem. 1989, 10, 186.
23. T. Fujita, Biosci. Biotech. Biochem. 1996, 60, 557.
24. B. C. Elmes, Aust. J. Chem. 1996, 49, 573.
25. G. Menichi, J. Het. Chem. 1984, 21, 209.
26. D. Galanakis, C. A. Davis, B. D. R. Herrero, C. R. Ganellin, P. M. Dunn, D. H. Jenkinson, J. Med. Chem. 1995, 38, 595.
27. J. H. Lister, J. Chem. Soc. 1960, 3394.
28. (a) T. Jojima, H. Takeshiba, T. Kinito, Y. Kondo, Annu. Rep. Sankyo Res. Lab. 1980, 32, 114.
29. (b) T. Jojima, H. Takeshiba, T. Kinito, Y. Kondo, Annu. Rep. Sankyo Res. Lab. 1966, 9, 423.
30. D. Gosh, J. Med. Chem. 1966, 9, 423.
31. E. P. Greenberg, Nature 2000, 406, 947. doi: 10.1038/35023203
32. T. Ikeda, A. Ledwith, C. H. Bamford, R. A. Hann, Biochim. Biophys. Acta 1984, 769, 57. doi: 10.1016/0005-2736(84)90009-9
33. Figure courtesy of Avecia Inc (http://www.avecia.com)
34. F. Gasparrini, M. O. Tinti, M. Santaniello, N. Scafetta, G. Gallo, L. Critelli, P. Foresta, in New Antimicrobial Agents: Synthesis and Structure-Activity Relationship, in QSAR and Molecular Modelling: Concepts, Computational Tools and Biological Applications (Eds. F. Sanz, J. Giraldi, F. Manaut) 1995, p. 193 (Prous Scientific: Barcelona).
35. H. Tsubouchie, K. Ohgura, K. Yasumura, H. Ishikawa, M. Kikuchi, Bioorg. Med. Chem. Lett. 1997, 7, 1721. doi: 10.1016/S0960-894X(97)00297-7
36. T. Kuyyakanond, L. B. Quesnel, FEMS Microbiol. Lett. 1992, 79, 211. doi: 10.1016/0378-1097(92)90211-6
37. J. A. Chawner, P. Gilbert, J. Appl. Bacteriol. 1989, 66, 253.
38. V. Vuddhakul, J. Antimicrob. Chemother. 1988, 21, 755.
39. V. D. Warner, D. M. Lynch, R. S. Ajemian, J. Pharm. Sci. 1976, 65, 1070.
40. S. R. Ernst, F. W. Cagle, Acta Crystallogr. 1977, B33, 235.
41. Tripos Associates (http://www.tripos.com).
42. Biobyte Corporation (http://www.biobyte.com).
43. G. E. Kellogg, S. F. Semus, D. J. Abraham, J. Comput. Aided Mol. Des. 1991, 5, 545.
44. J. G. Topliss, R. P. Edwards, J. Med. Chem. 1979, 22, 1238.
45. University of Georgia SPARC calculator (http://ibmlc2.chem.uga.edu/sparc/index/cfm).
46. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, 1972 (Butterworths: London).