Novel anti-bacterials against MRSA: Synthesis of focussed combinatorial libraries of tri-substituted 2(5H)-furanones

Current Drug Discovery Technologies

Volumn 3, Issue 2, 2006, Pages 125-134

  Lattmann, Eric ^a   Sattayasai, Nison ^b   Schwalbe, Carl S ^a   Niamsanit, Suwanna ^b   Billington, David C ^a   Lattmann, Pornthip ^a   Langley, Christopher A ^a   Singh, Harjit ^a   Dunn, Simon ^a  

^a ASTON UNIVERSITY   (United Kingdom)

^b Khon Kaen University   (Thailand)

Author keywords

4 amino 5 alkoxy 2(5H) furanones; Antibacterials; Benzimidazolyl lead structure; Butenolides; Focussed combinatorial library; MRSA

Indexed keywords

3 BROMO 5 ALKOXY 4 AMINO 2(5H) FURANONE DIVATIVE; 3 HALOGEN 4 AMINO 5 ALKOXY 2(5H) FURANONE DERIVATIVE; ALCOHOL; AMINE; ANTIINFECTIVE AGENT; BENZIMIDAZOYLYL FURANONE DERIVATIVE; BUTENOLIDE; FURAN DERIVATIVE; MUCOBROMIC ACID; MUCOCHLORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

ANTI-BACTERIAL AGENTS; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; DRUG RESISTANCE, MULTIPLE, BACTERIAL; ESCHERICHIA COLI; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TECHNOLOGY, PHARMACEUTICAL;

EID: 33747870835     PISSN: 15701638     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016306778108857     Document Type: Article

References (31)

1. De Rosa M., Giordano S., Scettri A., Sodano G., Soriente A., Pastor P.G., Alcaraz M. J., Payá M.: Synthesis and Comparison of the Antiinflammatory activity of manoalide and cacospongionolide B analogues. J. Med. Chem. 41, 3232-3238, (1998);
2. Coombs J., Lattmann E., Hoffmann H. M. R.: Total synthesis of manoalide. Synthesis 1367-1371, (1998).
3. Lattmann E., Coombs J., Hoffmann H. M. R.: Pyranofuranones via lewis acid mediated hetero-Diels-Alder reactions of 4-Furan-2(5H)-ones. A convergent route to the manoalide substructure. Synthesis 171-177, (1996).
4. 2 by the marine natural products manoalide, Luffariellolide and scalaradial. J. Am. Chem. Soc. 114, 5093-5100, (1992).
5. 2-butenolides). Synthesis 164-170, (1996).
6. Terrett N. K., Gardner M., Gordon D. W., Kobylecki R. J., Steele J.: Combinatorial synthesis-The Design of compound libraries and their application to drug discovery. Tetrahedron 51, 8135-8173, (1995);
7. Thompson L.A., Ellman J.A.: Synthesis and applications of small molecule libraries. Chem. Rev. 96, 555-600, (1996);
8. Ellingboe J.W.: Combinatorial chemistry methodology and combinatorial library design. Med. Chem. Res. 8, 181-186, (1998);
9. Czarnik A.W., Keene J.D.: Combinatorial chemistry. Curr. Biol. 20, 705-707, (1998).
10. Lam K. S., Lebl M., Krchñák V.: The "one-bead-one- compound" combinatorial library method. Chem. Rev., 97, 411-447, (1997);
11. Pirrung M. C.: Spatially addressable combinatorial libraries. Chem. Rev. 79, 473-488, (1997);
12. Kerwin J. F.: Combinatorial technologies: Prospects and future issues. Comb. Chem. Mol. Divers. Drug Discov. 475-481, (1998).
13. 2-butenolides). Synthesis 164-170, (1996).
14. Lattmann E., Billington D.C., Langley C.A.: Synthesis of combinatorial libraries of 3,4,5-substitutes 2(5H)-furanones. Part one: Construction of a sub-library of halogenated 5-alkoxy-2(5H)-furanones. Drug Design Discov. 16, 237-242, (1999);
15. Lattmann E., Billington D.C., Langley C. A.: Synthesis of combinatorial libraries of 3,4,5-substitutes 2(5H)-furanones. Part two: Construction of a library of 4-amino-5-alkoxy-2(5H)-furanones. Drug Design Discov. 16, 243-250, (1999).
16. 2-butenolides. J. Org. Chem. 29, 137-139, (1964).
17. Martín M. R., Mateo A. I.: Synthesis of new homochiral polyfunctionalized furan-2(5H)-ones. Tetrahedron Asymmetry 5, 1385-1392, (1994).
18. Mowry D. T.: Mucochloric acid. I. reactions of the pseudo acid group. J. Am. Chem. Soc. 72, 2535-2537, (1950).
19. Feringa B. L., de Lange B., Jansen L. F., de Jong J. C., Lubben M., Faber W., Schudde E. P.: Asymmetric 1,4-additions to 5-alkoxy-2(5H)-furanones. Enantio-selective synthesis and absolute configuration. Pure Appl. Chem. 64, 1865-1882, (1992).
20. Fariña F., Martín M. V., Sánchez F., Maestro M. C., Martín M. R.: Pseudoesters and derivatives; XVII. Synthesis of 4-Alkylamino- and 4-Alkylthio-5-methoxyfuran-2(5H)-ones. Synth. Commun. 5, 397-398, (1983).
21. Jähnisch K., Duczek W.: Reaktionen von mucochlorsäurederivaten mit Anilin. J. Prakt. Chem. 332, 117-121, (1990).
22. Ducher S., Michet A.: Action de nucléophiles sulfurés sur le dichloro-2,3 butène-2 olide-4. Bulletin de la Société de Chimique de France, 11, 1923-1928, (1976);
23. Fishbein P.L., Moore H.W.: Chlorocyanoketene. Synthesis and cycloadditions to alkenes. J. Org. Chem. 49, 2190-2914, (1984).
24. Boukouvalas J., Lachance N., Ouellet M., Trudeau M.: Facile Access to 4-Aryl-2(5H)-furanones by suzuki cross coupling: Efficient synthesis of rubrolides C and E. Tetrahedron Lett. 39, 7665-7668, (1998).
25. Gravert D. J., Janda K. D.: Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies. Chem. Rev. 97, 489-509, (1997).
26. Lattmann E., Kinchington D., Singh H., Merino I., Begum A., Ayuko W., Tisdale M.J.: Synthesis of simple and bis-cyclic 3,4-dihalogenated 2(5H)-furanones and their evaluation as novel cytotoxic agents. Pharm. Pharm. Lett. 11, 5-8, (2001).
27. Lattmann E., Hoffmann H. M. R.: From tetronic Acid and furfural to C(4)-halogenated, vinylated and formylated furan-2(5H)-ones and their 5-alkoxy derivatives. Synthesis 155-163, (1996).
28. Rossi R., Bellina F., Biagetti M., Mannina L.: Selective palladium-mediated synthesis of racemic 4,5-disubstituted 5H-furan-2-ones from 3-ynic acids and organic halides. Tetrahedron Lett. 39, 7599-7602, (1998).
29. Allen F. H., Kennard O., Watson D. G., Brammer L., Orpen A. G., Taylor R. J. Chem. Soc. Perkin Trans. II, S1, (1987).
30. th ed., CRC Press, Boca Raton, FL pp. 8-48, (2004).
31. Tamm I., Folker K., Shunk C. H.: Certain benzimidazoles, benzenes and ribofuranosylpurines as inhibitors of influenza B virus multiplication. J. Bacteriol. 72, 59-64, (1956).