A versatile annulation protocol toward novel constrained phosphinic peptidomimetics

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7222-7228

  Nasopoulou, Magdalini ^a   Georgiadis, Dimitris ^a   Matziari, Magdalini ^a   Dive, Vincent ^b   Yiotakis, Athanasios ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b DIF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPHOSPHINIC ACIDS; AZACYCLIC RING SYSTEM; PEPTIDOMIMETICS; PHOSPHINIC SCAFFOLDS;

BIOMATERIALS; PEPTIDES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

ALDEHYDE DERIVATIVE; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC DERIVATIVE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; AMINO ACIDS; CYCLIZATION; FLUORENES; PEPTIDES; PHOSPHINIC ACIDS; PIPECOLIC ACIDS;

EID: 34548781836     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071081l     Document Type: Article

References (38)

1. Velazquez-Campoy, A.; Luque, I.; Freire, E. Thermochim. Acta 2001, 380, 217.
2. For reviews, see: (a) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
3. (b) Gante, J. Angew. Chem., Int. Ed. 1994, 33, 1699.
4. (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
5. For a molecular dynamics study on phosphinic cyclic hexapeptides, see: Cuniasse, P.; Raynal, I.; Lecoq, A.; Yiotakis, A.; Dive, V. J. Med. Chem. 1995, 38, 553.
6. For reviews, see: (a) Dive, V.; Lucet-Levannier, K.; Georgiadis, D.; Cotton, J.; Vassiliou, S.; Cuniasse, P.; Yiotakis, A. Biochem. Soc. Trans. 2000, 28, 455.
7. (b) Collinsová, M.; Jiráček, J. Curr. Med. Chem. 2000, 7, 629.
8. (c) Yiotakis, A.: Georgiadis, D.; Matziari, M.; Makaritis, A.; Dive, V. Curr. Org. Chem. 2004, 8, 1135.
9. (d) Dive, V.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A. Cell. Mol. Life Sci. 2004, 61, 2010.
10. Selected examples: (a) Jiráček, J.; Yiotakis, A.; Vincent, B.; Checler, F.; Dive, V. J. Biol. Chem. 1996, 271, 19606.
11. (b) Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiráček, J.; Vazeux, G.; Chauvet, M.-T.; Cuniasse, P.; Corvol, P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330.
12. (c) Georgiadis, D.; Vazeux, G.; Llorens-Cortes, C.; Yiotakis, A.; Dive, V. Biochemistry 2000, 39, 1152.
13. (d) Georgiadis, D.; Beau, F.; Czarny, B.; Cotton, J.; Yiotakis, A.; Dive, V. Circ. Res. 2003, 93, 148.
14. (e) Matziari, M.; Beau, F.; Cuniasse, P.; Dive, V.; Yiotakis, A. J. Med. Chem. 2004, 47, 325.
15. Hanessian, S.; MacKay, D. B.; Moitessier, N. J. Med. Chem. 2001, 44, 3074.
16. Cuniasse, P.; Devel, L.; Makaritis, A.; Beau, F.; Georgiadis, D.; Matziari, M.; Yiotakis, A.; Dive, V. Biochimie 2005, 87, 393.
17. Devel, L.; Rogakos, V.; David, A.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A.; Dive, V. J. Biol. Chem. 2006, 281, 11152.
18. Yiotakis, A.; Vassiliou, S.; Jiráček, J.; Dive, V. J. Org. Chem. 1996, 61, 6601.
19. (a) Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334.
20. (b) Hanessian, S.; Sailes, H.; Therrien, E. Tetrahedron 2003, 59, 7047.
21. (c) Manzoni, L.; Colombo, M.; Scolastico, C. Tetrahedron Lett. 2004, 45, 2623.
22. For studies on the related 3-component condensation of aldehydes, carbamates, and phosphinic acids, see: (a) Chen, S.; Coward, J. K. Tetrahedron Lett. 1996, 37, 4335.
23. (b) Matziari, M.; Yiotakis, A. Org. Lett. 2005, 7, 4049.
24. See the Supporting Information for the synthesis of the precursor Fmoc-protected aminoalcohols.
25. (a) Gage, J.; Evans, D. Organic Syntheses; Wiley: New Nork, 1993; Collect. Vol. VIII, p 528.
26. (b) Carocci, A.; Catalano, A.; Corbo, F.; Duranti, A.; Amoroso, R.; Franchini, C.; Lentini, G.; Tortorella, V. Tetrahedron: Asymmetry 2000, 11, 3619.
27. (c) Damm, W.; Hoffmann, U.; Macko, L.; Neuburger, M.; Zehnder, M.; Giese, B. Tetrahedron 1994, 50, 7029.
28. Soroka, M. Liebigs Ann. Chem. 1990, 331.
29. (a) Parr, I. B.; Boehlein, S. K.; Dribben, A. B.; Schuster, S. M.; Richards, N. G. C. J. Med. Chem. 1996, 39, 2367.
30. (b) Gu, X.; Tang, X.; Cowell, S.; Ying, J.; Hruby, V. J. Tetrahedron Lett. 2002, 43, 6669.
31. Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66, 6604.
32. Nasopoulou, M.; Matziari, M.; Dive, V.; Yiotakis, A. J. Org. Chem. 2006, 71, 9525.
33. Makaritis, A.; Georgiadis, D.; Dive, V.; Yiotakis, A. Chem. Eur. J. 2003, 9, 2079.
34. For a review, see: Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
35. Xiong, H.; Huang, J.; Ghosh, S. K.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694.
36. Kokotos, G.; Padron, J. M.; Martin, T.; Gibbons, W. A.; Martin, V. S. J. Org. Chem. 1998, 63, 3741.
37. See the Supporting Information for HPLC experimental conditions.
38. Buchschacher, P.; Cassal, J. M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1977, 60, 2747.