Syntheses, structural and antimicrobial studies of a new N-allylamide of monensin A and its complexes with monovalent metal cations

Tetrahedron

Volumn 65, Issue 36, 2009, Pages 7730-7740

  Łowicki, Daniel ^a   Huczyński, Adam ^a   Stefańska, Joanna ^b   Brzezinski, Bogumil ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Antibacterial activity; Complexes; Hydrogen bonds; Ionophores; Monovalent cations

Indexed keywords

LITHIUM ION; MONENSIN A; MONENSIN DERIVATIVE; POTASSIUM ION; SODIUM ION; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GRAM POSITIVE BACTERIUM; HYDROGEN BOND; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

POSIBACTERIA;

EID: 67949097540     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.077     Document Type: Article

References (43)

1. Haney Jr. M.E., and Hoehn M.M. Antimicrob. Agents Chemother. 7 (1967) 349-352
2. Westley J.W., Evans R.H., Sello L.H., Troupe N., Liu C., and Miller P.A. J. Antibiot. 34 (1981) 1248-1252
3. Pospisil S., Sedmera P., and Havlicek V. J. Antibiot. 49 (1996) 935-937
4. Lutz W.K., Winkler F.K., and Dunitz J.D. Helv. Chim. Acta 54 (1971) 1103-1108
5. Martinek T., Riddell F.G., Wilson C., and Weller C.T. J. Chem. Soc., Perkin Trans. 2 (2000) 35-41
6. Duax W.L., Smith G.D., and Strong P.D. J. Am. Chem. Soc. 102 (1980) 6725-6729
7. Ward D.L., Wei K.T., Hoogerheide J.C., and Popov A.I. Acta Crystallogr., Sect. B 34 (1978) 110-115
8. Huczyński A., Ratajczak-Sitarz M., Katrusiak A., and Brzezinski B. J. Mol. Struct. 832 (2007) 84-89
9. Huczyński A., Ratajczak-Sitarz M., Katrusiak A., and Brzezinski B. J. Mol. Struct. 871 (2007) 92-97
10. Huczyński A., Ratajczak-Sitarz M., Katrusiak A., and Brzezinski B. J. Mol. Struct. 888 (2008) 224-229
11. Pedersen C.J. J. Am. Chem. Soc. 89 (1967) 7017-7036
12. Pedersen C.J. Angew. Chem., Int. Ed. Engl. 27 (1988) 1021-1027
13. Gokel G.W. Encyclopedia of Supramolecular Chemistry: Crown Ethers (2004), Marcel Dekker, Boca Raton, FL, USA pp 326-333
14. Mollenhauer H.H., Morre D.J., and Rowe L.D. Biochim. Biophys. Acta 1031 (1990) 225-246
15. Nakazato K., and Hatano Y. Biochim. Biophys. Acta 1064 (1991) 103-110
16. Riddell F.G. Chirality 14 (2002) 121-125
17. Stephan B., Rommel M., Daugschies A., and Haberkorn A. Vet. Parasitol. 69 (1997) 19-29
18. Butaye P., Devriese L.A., and Haesebrouck F. Clin. Microbiol. Rev. 16 (2003) 175-188
19. Westley J.W., Liu C., Evans R.H., Sello L.H., Troupe N., and Hermannn T. J. Antibiot. 36 (1983) 1195-1200
20. Huczyński A., Przybylski P., Brzezinski B., and Bartl F. Biopolymers 81 (2006) 282-294
21. Huczyński A., Przybylski P., Brzezinski B., and Bartl F. Biopolymers 82 (2006) 491-503
22. Huczyński A., Michalak D., Przybylski P., Brzezinski B., and Bartl F. J. Mol. Struct. 797 (2006) 99-110
23. Huczyński A., Michalak D., Przybylski P., Brzezinski B., and Bartl F. J. Mol. Struct. 828 (2007) 130-141
24. Huczyński A., Łowicki D., Brzezinski B., and Bartl F. J. Mol. Struct. 874 (2008) 89-100
25. Huczyński A., Przybylski P., and Brzezinski B. Tetrahedron 63 (2007) 8831-8839
26. Huczyński A., Łowicki D., Brzezinski B., and Bartl F. J. Mol. Struct. 879 (2008) 14-24
27. Huczyński A., Przybylski P., and Brzezinski B. J. Mol. Struct. 788 (2006) 176-183
28. Huczyński A., Przybylski P., Schroeder G., and Brzezinski B. J. Mol. Struct. 29 (2007) 111-119
29. Huczyński A., Brzezinski B., and Bartl F. J. Mol. Struct. 886 (2008) 9-16
30. Huczyński A., Przybylski P., Brzezinski B., and Bartl F. J. Phys. Chem. B 110 (2006) 15615-15623
31. Huczyński A., Stefańska J., Przybylski P., Brzezinski B., and Bartl F. Bioorg. Med. Chem. Lett. 18 (2008) 2585-2589
32. Huczyński A., Domańska A., Paluch I., Stefańska J., Brzezinski B., and Bartl F. Tetrahedron Lett. 49 (2008) 5572-5575
33. Huczyński A., Domańska A., Łowicki D., Brzezinski B., and Bartl F. J. Mol. Struct. 920 (2009) 414-423
34. Łowicki D., Huczyński A., Ratajczak-Sitarz M., Katrusiak A., Stefańska J., Brzezinski B., and Bartl F. J. Mol. Struct. 923 (2009) 53-59
35. Lopes N.P., Stark C.B.W., Gates P.J., and Staunton J. Analyst 127 (2002) 503-506
36. Kiehl D.E., Julian R.K., and Kennington A.S. Rapid Commun. Mass Spectrom. 12 (1998) 903-910
37. Lopes N.P., Stark C.B.W., Hong H., Gates P.J., and Staunton J. Rapid Commun. Mass Spectrom. 16 (2002) 414-420
38. Stewart J.J.P. J. Comput. Chem. 10 (1989) 209-220
39. Stewart J.J.P. J. Comput. Chem. 12 (1991) 320-341
40. CAChe 5.04 UserGuide (2003), Fujitsu, Beaverton, Oregon
41. Przybylski P., Huczyński A., and Brzezinski B. J. Mol. Struct. 826 (2007) 156-164
42. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Disc Susceptibility Tests; Approved Standard M2-A9 (2006), Clinical and Laboratory Standards Institute, Wayne, PA, USA
43. Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M7-A7 (2006), Clinical and Laboratory Standards Institute, Wayne, PA, USA