The Hetero Diels-Alder approach to carbohydrate-containing molecular scaffolding

Current Organic Synthesis

Volumn 4, Issue 1, 2007, Pages 47-57

  Cacciarini, Martina ^a   Menichetti, Stefano ^a   Nativi, Cristina ^a   Richichi, Barbara ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbohydrate containing scaffolds; Chinese hamster ovary (CHO); Heteronuclear single quantum coherence; Matrix metalloelastase 12; Neurokinin A; NMR spectroscopy

Indexed keywords

EID: 33947104505     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017907779981570     Document Type: Review

References (32)

1. Hirschmann, R.; Nicolaou, K.C.; Pietranico, S.; Salvino, J.; Leahy, E.M.; Sprengeler, P.A.; Furst, G.; Smith III, A.B.; Strader, C.D.; Cascieri, M.R.; Candelore, M.R.; Donaldson, C.; Vale, W.; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217.
2. Hirschmann, R.; Nicolaou, K.C.; Pietranico, S.; Leahy, E.M.; Salvino, J.; Arison, B.; Cichy, M.A.; Spoors, P.G.; Shakespeare, W.C.; Sprengeler, P.A.; Hamley, P.; Smith III, A.B.; Reisine, T.; Raynor, K.; Maechler, L.; Donaldson, C.; Vale, W.; Freidinger, R.M.; Cascieri, M.R.; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550.
3. a) Sofia, M.J. Med. Chem. Res., 1998, 8(7/8), 362;
4. b) Thanh, G.; Abbenante, G.; Becker, B.; Grathwohl, M.; Halliday, J.; Tometzki, G.; Zuegg, J.; Meutermans, W. DDT, 2003, 8, 701.
5. a) Capozzi, G.; Franck, R.W.; Mattioli, M.; Menichetti, S.; Nativi, C.; Valle, G.; J. Org. Chem., 1995, 60, 6416;
6. Win, W.W.; Franck, R.W. J. Org. Chem., 1997, 62, 4510.
7. Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C.; Raffaelli, B. Chem. Eur. J., 1999, 5, 1748.
8. a) Capozzi, G.; Dios, A.; Franck, R.W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tabarez, M. Angew. Chem. Int. Ed. Engl., 1996, 108, 805;
9. b) Marzabadi, C.H.; Franck, R.W.; Schinazi, R.F. Bioorg. Med. Chem, 2002, 10, 273.
10. Capozzi, G.; Catelani, G.; D'Andrea, F.; Menichetti, S.; Nativi, C. Carb. Res., 2003, 338, 123.
11. Capozzi, G.; Nativi, C.; Bartolozzi, A.; Falciani, C.; Menichetti, S.; Paolacci, A. J. Org. Chem., 1999, 64, 6490.
12. Capozzi, G.; Corti, A.; Menichetti, S.; Nativi, C. Tetrahedron Lett. 1997, 38, 5041.
13. Capozzi, G.; Falciani, C.; Franck, R.W.; Menichetti, S.; Nativi, C. Tetrahedron Lett., 1995, 36, 6755.
14. Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett., 1994, 35, 4591.
15. Somsak, L.; Nemeth, I. J. Carbohydr. Chem., 1993, 12, 679.
16. Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C. J. Org. Chem., 1997, 62, 2611.
17. Capozzi, G.; Giannini, S.; Menichetti, S.; Nativi, C.; Giolitti, A.; Patacchini, R.; Perrotta, E.; Altamura, M.; Maggi, C.A. Bioorg. Med. Chem. Lett., 2002, 12, 2263.
18. Giolitti, A.; Cucchi, P.; Renzetti, A.R.; Rotondaro, L.; Zappitelli, S.; Maggi, C.A. Neuropharmacology, 2000, 39, 1422.
19. Munson, P.J.; Rodband, D. Anal. Biochem., 1980, 107, 220.
20. Venturi, F.; Venturi, C.; Liguori, F.; Cacciarini, M.; Montalbano, M.; Nativi, C. J. Org. Chem., 2004, 69, 6153.
21. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem., 1978, 43, 2087.
22. a) Boccardo, G.; Capozzi, G.; Giuntini, M.; Menichetti, S.; Nativi, C. Tetrahedron, 1997, 53, 17383;
23. b) Tamarez, M.M.; Franck, R.W.; Geer, A. Tetrahedron, 2003, 59, 4249.
24. König, W.; Geiger, R. Chem. Ber., 1970, 103, 788.
25. Sheehan, J.C.; Ledis, S.L. J. Am. Chem. Soc., 1973, 95, 875.
26. Alzeer, J.; Vasella, A. Helv. Chim. Acta, 1995, 78, 177.
27. Wittaker, M.; Floyd, C.D.; Brown, P.; Gearing, A.J. Chem Rev., 1999, 99, 27.
28. Fragai, M.; Nativi, C.; Richichi, B.; Venturi, C. Chembiochem, 2005, 6, 1345.
29. All MMPs are characterized by an hydrophobic cavity, conventionally designed as S1' pocket. In the case of MMP-12, the wide S1' pocket is able to accommodate relatively large hydrophobic groups and to provide an appreciable interaction with the protein.
30. Knight, C.G.; Willenbrock, F.; Murphy, G. FEBS Lett., 1992, 296, 263.
31. For the inhibitory activity of biphenyl derivatives see: Hajduk, P.J.; Sheppard, G.; Nettesheim, D.G.; Olejniczak, E.T.; Shuker, S.B.; Meadows, R.P.; Steinman, D.H.; Carrera, G.M. Jr.; Marcotte, P.A.; Severin, J.; Walter, K.; Smith, H.; Gubbins, E.; Simmer, R.; Holzman, T.F.; Morgan, D.W.; Davidsen, S.K.; Summers, J.B.; Fesik, S.W. J. Am. Chem. Soc. 1997, 119, 5818.
32. Boger, D.L.; Corbett, W.L. J. Org. Chem., 1992, 57, 4777.