Synthesis of new semi-synthetic dipodands and tripodands from naturally occurring polyether ionophores

Tetrahedron Letters

Volumn 49, Issue 39, 2008, Pages 5572-5575

  Huczyński, Adam ^a   Domańska, Agata ^a   Paluch, Izabela ^a   Stefańska, Joanna ^b   Brzezinski, Bogumil ^a   Bartl, Franz ^c  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

^c CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

Antimicrobial activity; Ionophores; Lasalocid; Monensin; Podands; Synthesis

Indexed keywords

IONOPHORE; LASALOCID; MONENSIN; POLYETHER;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA PARAPSILOSIS; CONTROLLED STUDY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 49249090962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.116     Document Type: Article

References (26)

1. Maia A., Landini D., Leska B., and Schroeder G. Tetrahedron Lett. 44 (2003) 4149-4151
2. Avallone E., Izzo I., Vuolo G., Costabile M., Garrisi D., Pasquato L., Scrimin P., Tecilla P., and De Riccardis F. Tetrahedron Lett. 32 (2003) 6121-6124
3. Leska B., Pankiewicz R., Schroeder G., and Maia A. Tetrahedron Lett. 47 (2006) 5673-5676
4. Maia A., Landini D., Leska B., and Schroeder G. Tetrahedron 60 (2004) 10111-10115
5. Maia A., Landini D., Betti C., Leska B., and Schroeder G. New J. Chem. 29 (2005) 1195-1198
6. Ferdani R., and Gokel G.W. Encyclopedia of Supramolecular Chemistry: Ionophores (2004), Marcel Dekker pp 760-766
7. Westley J.W. Polyether Antibiotics. Naturally Occurring Acid Ionophores Vol. 1 (1982), Marcel Dekker, New York pp 1-20
8. Pressman B.C. Antibiotics and Their Complexes (1985), Marcel Dekker, New York pp 1-18
9. Westley J.W. Polyether Antibiotics. Naturally Occurring Acid Ionophores Vol. 2 (1983), Marcel Dekker, New York pp 51-86
10. Dutton C.J., Banks B.J., and Cooper C.B. Nat. Prod. Rep. 12 (1995) 165-181
11. Huczyński A., Ratajczak-Sitarz M., Katrusiak A., and Brzezinski B. J. Mol. Struct. 871 (2007) 92-97
12. Huczyński, A.; Ratajczak-Sitarz, M.; Katrusiak, A.; Brzezinski, B. J. Mol. Struct., in press. doi:10.1016/j.molstruc.2007.12.005.
13. Huczyński A., Ratajczak- Sitarz M., Katrusiak A., and Brzezinski B. J. Mol. Struct. 832 (2007) 84-89
14. Pinkerton M., and Steinrauf L.K. J. Mol. Biol. 49 (1970) 533-546
15. Suh I.-H., Aoki K., and Yamazaki H. Acta Crystallogr., Sect. C 45 (1989) 415-418
16. Shui X., and Eggleston D.S. Acta Crystallogr., Sect. C 51 (1995) 805-809
17. Westley J.W., Evans R.H., and Blount J.F. J. Am. Chem. Soc. 99 (1977) 6057-6061
18. Tsukube H., and Sohmiya H. Tetrahedron Lett. 31 (1990) 7027-7030
19. Synthesis of Monensin A (6) (or Lasalocid acid (1)): Monensin A sodium salt (Fluka) (or Lasalocid sodium salt from Avatec (Fa. Spezialfutter Neuruppin)) was dissolved in dichloromethane and stirred vigorously in the presence of aqueous sulfuric acid (40 ml) (pH 1.5). The organic layer containing 6 (or 1) was washed with distilled water, and the dichloromethane was evaporated under reduced pressure.
20. Representative procedure for (5): A mixture of 1,3,5-tris(bromomethyl)benzene (Aldrich) (45 mg, 0.125 mmol), Lasalocid acid (1) (443 mg, 0.75 mmol), DBU (137 mg, 0.9 mmol) and 40 ml of toluene was heated at 90 °C for 5 h. After cooling, the precipitated DBU-hydrobromide (DBU·HBr) was filtered and washed with hexane. The filtrate and the washings were combined and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (Fluka type 60) to give 5 (160 mg, 68% yield) as a colourless oil showing a tendency to form a glass state. Compounds 2-4 and 7-9 were obtained according to Scheme 1.
21. 24: C, 70.67; H, 8.98. Found: C, 70.42; H, 9.13.
22. Huczyński A., Pospieszny T., Wawrzyn R., Ratajczak-Sitarz M., Katrusiak A., Brzezinski B., and Bartl F. J. Mol. Struct. 877 (2008) 105-114
23. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Disc Susceptibility Tests; Approved Standard M2-A9. Clinical and Laboratory Standards Institute, Wayne, PA, USA, 2006.
24. Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M7-A7. Clinical and Laboratory Standards Institute, Wayne, PA, USA, 2006.
25. The micro-organisms used in the tests were the following: Gram-positive cocci: Staphylococcus aureus NCTC 4163, Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 6538, Staphylococcus aureus ATCC 29213, Staphylococcus epidermidis ATCC 12228, Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 11778, Enterococcus hirae ATCC 10541, Micrococcus luteus ATCC 9341, Micrococcus luteus ATCC 10240, gram-negative rods: Escherichia coli ATCC 10538, Escherichia coli ATCC 25922, Escherichia coli NCTC 8196, Proteus vulgaris NCTC 4635, Pseudomonas aeruginosa ATCC 15442, Pseudomonas aeruginosa NCTC 6749, Pseudomonas aeruginosa ATCC 27853, Bordetella bronchiseptica ATCC 4617 and yeast-like organisms: Candida albicans ATCC 10231, Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019. The micro-organisms used here were provided by the Department of Pharmaceutical Microbiology, Medical University of Warsaw, Poland. The antimicrobial activities of the studied compounds were performed according to the method given in Ref. 16.
26. Huczyński A., Stefańska J., Przybylski P., Brzezinski B., and Bartl F. Bioorg. Med. Chem. Lett. 18 (2008) 2585-2589