6-Oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 20, 1999, Pages 2947-2952

  Kanojia, Ramesh M ^a   Murray, William ^a   Bernstein, Jeffrey ^a   Fernandez, Jeffrey ^a   Foleno, Barbara D ^a   Krause, Heather ^a   Lawrence, Laura ^a   Webb, Glenda ^a   Barrett, John F ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANACARDIC ACID; ANACARDIC ACID DERIVATIVE; ANTIINFECTIVE AGENT; HISTIDINE; PROTEIN KINASE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ENTEROCOCCUS FAECIUM; ENZYME INHIBITION; GRAM POSITIVE BACTERIUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; STAPHYLOCOCCUS AUREUS;

ANACARDIC ACIDS; ANTI-BACTERIAL AGENTS; BACTERIA; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; SALICYLIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); ENTEROCOCCUS FAECALIS; ENTEROCOCCUS FAECIUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 0033581637     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00508-9     Document Type: Article

References (43)

1. (a) Swartz, M. N. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2420.
2. (b) Tomasz, A. N. Engl. J. Med. 1994, 330, 1247.
3. (a) Kanojia, R. M.; Demers, J. P.; Fraga-Spano, S. A.; Guan, J.; Johnson, S. G.; Johnson, C. E., Macielag, M. J.; Ohemeng, K. A.; Russell, R. K.; Sheppard, C. M.; Sui, Z.; Weidner-Wells, M. A.; Werblood, H.; Bernstein, J.; Donetz, A.; Dow, T.; Foleno, B.; Goldschmidt, R.; Hilliard, J.; Lawrence, L.; Loeloff, M. and Barrett, J. F. Abstract of Papers, 214th ACS National Meeting, Las Vegas, 1997, Abst. #: MEDI-154.
4. (b) Weidner-Wells, M. A.; Bernstein, J. Chen, R. H. K.; Kanojia, R. M.; Klaubert, D. H.; Sheppard, C. M. and Barrett, J. F. Abstract of Papers, 214th ACS National Meeting, Las Vegas, 1997, Abst. # MEDI-148.
5. (c) Hlasta, D. J.; Demers, J.; Foleno, B.; Johnson, S.; Kanojia, R. M.; Klaubert, D.; Sheppard, C. M.; Fraga-Spano, S. A.; Weidner-Wells, M. A.; Barrett, J. F. Abstract Of Papers, 37th Int. Conf. On Antimicrobial Agents and Chemotherapy Meeting, Toronto 1997, Abst. # F- 227 .
6. (d) Macielag, M. J.; Bernstein, J.; Demers, J. P.; Dow, T.; Foleno, B.; Goldschmidt, R.; Guan, J.; Hilliard, J. J.; Hlasta, D. J.; Johnson, C. E.; Johnson, S. G.; Kanojia, R. M..; Loeloff, M.; Ohemeng, K. A.; Russell, R. K.; Sheppard, C. M.; Fraga-Spano, S. A.; Sui, Z.; Weidner-Wells, M. A.; Werblood, H. and Barrett, J. F. Abstract of Papers, 37th Interscience Conference on Antimicrobial Agents and Chemotheray Meeting, Toronto, 1997, Abst. # F-228.
7. (e) Barrett, J. F.; Goldschmidt, R. M.; Lawrence, L. E.; Foleno, B.; Chen, R.; Demers, J. P.; Johnson, S.; Kanojia, R.; Fernandez, J.; Bernstein, L.; Licata, A.; Donetz, S.; Huang, S.; Hlasta, D. J.; Macielag, M. J.; Ohemeng, K.; Frechrtte, R.; Frosco, M. B.; Klaubert, D. H.; Whiteley, J. M.; Wang, L.; Hoch, J. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5317.
8. (f) Macielag, M. J.; Demers, J. P.; Fraga-Spano, S. A.; Hlasta, D. J.; Johnson, S, G.; Kanojia, R. M.; Russell, R. K.; Sui, Z.; Weidner-Wells, M. A.; Werblood, H.; Foleno, B, D.; Goldscmidt, R. M.; Loeloff, M. J.; Webb, G. C.; Barrett, J. F. J. Med. Chem. 1998, 41, 2939.
9. (g) Sui, Z.; Guan, G.; Hlasta, D. J.; Macielag, M. J.; Foleno, B. D.; Goldschmidt, R. M.; Loeloff, M. J.; Webb, G. C.; Barrett, J. F. Bioorg. Med Chem. Lett. 1998, 8, 1929.
10. (h) Barrett, J. F.; Hoch, J. A. Antimicrob. Agents Chemother. 1998, 42, 1529.
11. (a) Two-Component Signal Transduction; Hoch, J. A., Silhavy, T. J., Eds.; ASM; Washington, D. C., 1995; pp 25-51.
12. (b) Parkinson, J. S. Cell 1993, 73, 857.
13. (c) Stock, J. B.; Stock, A. M.; Mottonen, J. M. Nature 1990, 344, 395.
14. (d) Hazelbauer, G. L.; Berg, H. C.; Matsumura, P. Cell 1993 73, 15.
15. Stock, J. B.; Ninfa, A. J.; Stock, A. M. Microbiol. Rev. 1989, 53, 450.
16. Existence of such TCS in lower eucaryotes such as yeast and fungi has recently been noted, eg, (a) Ota, I. M.; Varshavsky, A. Science 1993, 262, 566.
17. (b) Maeda, T.; Wurgler-Murphy, S. M.; Saito, H. Nature 1994, 369, 242.
18. (c) Crovello, C. S.; Furie, B. C.; Furie, B. Cell 1995, 82, 279.
19. (d) Alex, L. A.; Borkovich, K. A.; Simon, S. I. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3416.
20. (a) Roychoudhury, S.; Zielinski, N. A.; Ninfa, A. J.; Allen, N. E.; Jungheim, L. N.; Nicas, T. L; Chakrabarty, A. M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 965.
21. (b) Domagala, J. M.; Allessi, D.; Gracheck, S.; Huang, L.; Huband, M.; Olson, E.; Shapiro, M.; Sing, R.; Song, Y.; Van Bogelen, R.; Vo, D.; Wold, S. Abstract of Papers, 29th Central Regional Meeting, ACS, Midland, Michigan. 1997.
22. Tyman, J. H. P. Chem. Soc. Rev. 1979, 8, 499.
23. (a) Eichbaum, F.; Hauptmann, H.; Rothschild, H. Anais Assoc, Quim. Brasil 1945, 4, 83.
24. (b) Biswas, A.K.; Roy, A. B. Nature 1958, 182, 1299.
25. (c) Gellerman, J. L; Walsh, N. J.; Werner, N. K.; Schlenk, H. Can. J. Microbiol. 1969, 15, 1219.
26. (d) Chatopadhyaya, M. K.; Khare, R. L.; Indian J. Pharm. 1970, 32, 46.
27. (e) Dutta, D.; Khare, R. L. Indian J. Pharm. 1971, 33, 112.
28. (f) Adwadkar, P. D.; El Sohly, M.Fitoterapia 1981, 52, 129.
29. (f) Himejima, M.; Kubo, I. J. Agric. Food Chem. 1991, 39, 418.
30. (g) Kubo, I.; Muroi, H; Hemejima, M. J. Agric. Food Chem. 1993, 41, 1016.
31. (h) Muroi, H.; Kubo, A.; Kubo, I. J. Agric. Food Chem. 1993, 41, 1780.
32. (i) Muroi, H.; Kubo, I. Biosci., Biotechnol, Biochem. 1994, 58, 1925.
33. (j) Corthout, J.; Pieters, L.; Claeys, M.; Geerts, St.; Vanden, B.; Vlietinck, A. Planta Med. 1994, 60, 460.
34. (k) Muroi, H.; Kubo, I. J. Appl. Bacteriol. 1996, 80, 387.
35. Prithviraj, B.;Manickam, M.; Singh, U. P.; Ray, A. B. Can. J. Bot. 1997, 75, 207.
36. 50 values are the mean of two experimental determinations.
37. This assay measures the ability of the test compound to inhibit autophosphorylation of NRII and/or transphosphorylation of NRI, the nitrogen regulatory TCS proteins from E. Coli.
38. Bass, R. J.; Banks, B. J.; Snrey, M. Tetrahedron Lett. 1980, 21, 769.
39. In vitro minimum inhibitory concentration against a panel of (a) Gram positive bacteria: S. aureus (ATCC29213), MRSA (OC2089) E. faecalis (OC3041). and E.faecium (OC3312 Van R),
40. (b) Gram- Negative bacteria: E. coli (OC2605, OC2530), K. pneumoniae (OC1943), P. aeruginosa (OC161, ATCC27853). Following the broth microdilution method of the National Committee for Clinical Laboratory Standards, determination of susceptibility was performed.
41. Compounds 14 and 15 were synthesized using the protocol described in Scheme 1. Compounds 16 and 17 were obtained from the Aldrich Library of Rare Compounds (SALOR). All the synthesized compounds (1-15) were characterized by NMR, IR, and MS spectra and CHN microanalyses.
42. Ingram, L. O.; Buttke, T. M. Adv. Microb. Physiol. 1984, 25, 253.
43. Hilliard, J.; Goldschmidt, R.; Licata, L.; Baum, E. Z.; Bush, K. Antimicrob. Agents Chemother. 1999, 43, 1693.