Synthesis of combinatorial libraries of 3,4,5-trisubstituted 2(5H)-furanones. Part one: Construction of a sub-library of halogenated 5-alkoxy-2(5H)-furanones

Drug Design and Discovery

Volumn 16, Issue 3, 1999, Pages 237-242

  Lattmann, Eric ^a   Billington, David C ^a   Langley, Christopher A ^a  

^a ASTON UNIVERSITY   (United Kingdom)

Author keywords

3,4 Dihalogen 2(5H) furanones; Anti cancer agent; Automated synthesis; Butenolides; Combinatorial chemistry; lead structure discovery

Indexed keywords

5 ALKOXY 2(5H) FURANONE; 5 HYDROXY 3,4 DIHALO 2(5H) FURANONE; 5 HYDROXY 4 CHLORO 2(5H) FURANONE; AMINE; FURANONE DERIVATIVE; FURFURAL; HALOGEN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION;

COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; FURANS; HALOGENS;

EID: 0032697781     PISSN: 10559612     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. De Rosa, M., Giordano, S., Seettri, A , Sodano, G., Soriente, A., Pastor, P. G , Alcaraz, M. J. and Payá, M. (1998). Synthesis and Comparison of the Antimflammatory Activity of Manoalide and Cacospongionolide B Analogues, J. Med Chem, 41, 3232-3238. Coombs, J., Lattmann, E. and Hoffmann, H. M. R. (1998). Total Synthesis of Manotiude. Synthesis, 1367-1371.
2. De Rosa, M., Giordano, S., Seettri, A , Sodano, G., Soriente, A., Pastor, P. G , Alcaraz, M. J. and Payá, M. (1998). Synthesis and Comparison of the Antimflammatory Activity of Manoalide and Cacospongionolide B Analogues, J. Med Chem, 41, 3232-3238. Coombs, J., Lattmann, E. and Hoffmann, H. M. R. (1998). Total Synthesis of Manotiude. Synthesis, 1367-1371.
3. Lattmann, E., Coombs, J and Hoffmann, H. M. R (1996). 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
4. 2 by the Marine Natural Products Manoalide, Luffanellolide and Scalaradial. J. Am. Chem Soc, 114, 5093-5100.
5. 2-butenolides), Synthesis. 164-170.
6. Terrett, N. K , Gardner, M , Gordon, D. W., Kobylecki. R. J. and Steele, J. (1995). Combinatorial Synthesis - The Design of Compound Libraries and their Application to Drug Discovery, Tetrahedron, 51, 8135-8173. Thompson, L. A. and Ellman, J. A. (1996). Synthesis and Applications of Small Molecule Libraries, Chem. Rev, 96, 555-600. Ellingboe, John, W. (1998). Combinatorial Chemistry Methodology and Combinatorial Library Design. Med. Chem. Res., 8, 181-186. Czarnik, A. W., Keene, J D. (1998). Combinatorial Chemistry. Curr. Biol , 20, 705-707.
7. Terrett, N. K , Gardner, M , Gordon, D. W., Kobylecki. R. J. and Steele, J. (1995). Combinatorial Synthesis - The Design of Compound Libraries and their Application to Drug Discovery, Tetrahedron, 51, 8135-8173. Thompson, L. A. and Ellman, J. A. (1996). Synthesis and Applications of Small Molecule Libraries, Chem. Rev, 96, 555-600. Ellingboe, John, W. (1998). Combinatorial Chemistry Methodology and Combinatorial Library Design. Med. Chem. Res., 8, 181-186. Czarnik, A. W., Keene, J D. (1998). Combinatorial Chemistry. Curr. Biol , 20, 705-707.
8. Terrett, N. K , Gardner, M , Gordon, D. W., Kobylecki. R. J. and Steele, J. (1995). Combinatorial Synthesis - The Design of Compound Libraries and their Application to Drug Discovery, Tetrahedron, 51, 8135-8173. Thompson, L. A. and Ellman, J. A. (1996). Synthesis and Applications of Small Molecule Libraries, Chem. Rev, 96, 555-600. Ellingboe, John, W. (1998). Combinatorial Chemistry Methodology and Combinatorial Library Design. Med. Chem. Res., 8, 181-186. Czarnik, A. W., Keene, J D. (1998). Combinatorial Chemistry. Curr. Biol , 20, 705-707.
9. Terrett, N. K , Gardner, M , Gordon, D. W., Kobylecki. R. J. and Steele, J. (1995). Combinatorial Synthesis - The Design of Compound Libraries and their Application to Drug Discovery, Tetrahedron, 51, 8135-8173. Thompson, L. A. and Ellman, J. A. (1996). Synthesis and Applications of Small Molecule Libraries, Chem. Rev, 96, 555-600. Ellingboe, John, W. (1998). Combinatorial Chemistry Methodology and Combinatorial Library Design. Med. Chem. Res., 8, 181-186. Czarnik, A. W., Keene, J D. (1998). Combinatorial Chemistry. Curr. Biol , 20, 705-707.
10. Lattmann, E. and Hoffmann, H. M. R. (1996). From Tetronic Acid and Furfural to C(4)-Halogenated, Vinylated and Formylated Furan-2(5H)-ones and Their 5-alkoxy Derivatives. Synthesis, 155-163.
11. Rossi, R , Bellina, F , Biagetti. M. and Mannina. L. (1998). 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. Boukouvalas, J , Lachance, N., Ouellet, M. and Trudeau, M. (1998) Facile Access to 4-Aryl-2(5H )-furanones by Suzuki Cross Coupling: Efficient Synthesis of Rubrolides C and E, Tetrahedron Lett, 39, 7665-7668
12. Rossi, R , Bellina, F , Biagetti. M. and Mannina. L. (1998). 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. Boukouvalas, J , Lachance, N., Ouellet, M. and Trudeau, M. (1998) Facile Access to 4-Aryl-2(5H )-furanones by Suzuki Cross Coupling: Efficient Synthesis of Rubrolides C and E, Tetrahedron Lett, 39, 7665-7668
13. 2-butenolides J. Org. Chem. 29, 137-139.
14. Martin, M. R. and Mateo, A. I. (1994). Synthesis of New Homochiral Polyfunctionalized Furan-2(5H)-ones. Tetrahedron Asymmetry, 5, 1385- 1392.
15. Mowry, D. T. (1950). Mucochloric Acid. I. Reactions of the Pseudo Acid Group, J. Am. Chem. Soc, 72, 2535-2537.
16. -1.
17. Lattmann, E. (1998). Halogenated Butenolides as Anti-Cancer Agents, (to Kanvir Research LTD.) Pat. Appl. Nr. 982476.8, UK-patent.