Development of a functionalizable external β-turn mimic based on a cis-fused 1,7-naphthyridine scaffold

European Journal of Organic Chemistry

Volumn , Issue 10, 2003, Pages 1868-1878

  Rombouts, Frederik J R ^a   De Borggraeve, Wim M ^a   Delaere, David ^a   Froeyen, Matheus ^a   Toppet, Suzanne M ^a   Compernolle, Frans ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Bioorganic chemistry; Conformation analysis; Cycloaddition; Naphthyridine; Peptidomimetics

Indexed keywords

AMIDE; AMINO ACID; DIPEPTIDE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; PERHYDRO 1,7 NAPHTHYRIDINE; PYRAZINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL MODEL; CONFORMATION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84961982788     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200652     Document Type: Article

References (50)

1. K.-C. Chou, Anal. Biochem. 2000, 286, 1-16 and references cited herein.
2. For leading reviews on β-turn mimics and peptidomimetics see: [2a] V. J. Hruby, P. M. Balse, Curr. Med. Chem. 2000, 7, 945-970. [2b] R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19. [2c] J. B. Ball, P. F. Alewood, J. Mol. Recognit. 1990, 3, 55-64. [2d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
3. For leading reviews on β-turn mimics and peptidomimetics see: [2a] V. J. Hruby, P. M. Balse, Curr. Med. Chem. 2000, 7, 945-970. [2b] R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19. [2c] J. B. Ball, P. F. Alewood, J. Mol. Recognit. 1990, 3, 55-64. [2d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
4. For leading reviews on β-turn mimics and peptidomimetics see: [2a] V. J. Hruby, P. M. Balse, Curr. Med. Chem. 2000, 7, 945-970. [2b] R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19. [2c] J. B. Ball, P. F. Alewood, J. Mol. Recognit. 1990, 3, 55-64. [2d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
5. For leading reviews on β-turn mimics and peptidomimetics see: [2a] V. J. Hruby, P. M. Balse, Curr. Med. Chem. 2000, 7, 945-970. [2b] R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19. [2c] J. B. Ball, P. F. Alewood, J. Mol. Recognit. 1990, 3, 55-64. [2d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
6. For some leading references on the incorporation of β-turn mimics see: [3a] R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks, R. Saperstein, Science 1980, 210, 656-658. [3b] M. G. Hinds, N. G. J. Richards, J. A. Robinson, J. Chem. Soc., Chem. Commun. 1988, 22, 1447-1449. [3d] M. Kahn, Synlett 1993, 3, 821-826. [3d] D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Burns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606. [3e] A. A. Virgilio, A. A. Bray, W. Zhang, L. Trinh, M. Snyder, M. M. Morrissey, J. A. Ellman, Tetrahedron 1997, 53, 6635-6644.
7. For some leading references on the incorporation of β-turn mimics see: [3a] R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks, R. Saperstein, Science 1980, 210, 656-658. [3b] M. G. Hinds, N. G. J. Richards, J. A. Robinson, J. Chem. Soc., Chem. Commun. 1988, 22, 1447-1449. [3d] M. Kahn, Synlett 1993, 3, 821-826. [3d] D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Burns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606. [3e] A. A. Virgilio, A. A. Bray, W. Zhang, L. Trinh, M. Snyder, M. M. Morrissey, J. A. Ellman, Tetrahedron 1997, 53, 6635-6644.
8. For some leading references on the incorporation of β-turn mimics see: [3a] R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks, R. Saperstein, Science 1980, 210, 656-658. [3b] M. G. Hinds, N. G. J. Richards, J. A. Robinson, J. Chem. Soc., Chem. Commun. 1988, 22, 1447-1449. [3d] M. Kahn, Synlett 1993, 3, 821-826. [3d] D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Burns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606. [3e] A. A. Virgilio, A. A. Bray, W. Zhang, L. Trinh, M. Snyder, M. M. Morrissey, J. A. Ellman, Tetrahedron 1997, 53, 6635-6644.
9. For some leading references on the incorporation of β-turn mimics see: [3a] R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks, R. Saperstein, Science 1980, 210, 656-658. [3b] M. G. Hinds, N. G. J. Richards, J. A. Robinson, J. Chem. Soc., Chem. Commun. 1988, 22, 1447-1449. [3d] M. Kahn, Synlett 1993, 3, 821-826. [3d] D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Burns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606. [3e] A. A. Virgilio, A. A. Bray, W. Zhang, L. Trinh, M. Snyder, M. M. Morrissey, J. A. Ellman, Tetrahedron 1997, 53, 6635-6644.
10. For some leading references on the incorporation of β-turn mimics see: [3a] R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks, R. Saperstein, Science 1980, 210, 656-658. [3b] M. G. Hinds, N. G. J. Richards, J. A. Robinson, J. Chem. Soc., Chem. Commun. 1988, 22, 1447-1449. [3d] M. Kahn, Synlett 1993, 3, 821-826. [3d] D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Burns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606. [3e] A. A. Virgilio, A. A. Bray, W. Zhang, L. Trinh, M. Snyder, M. M. Morrissey, J. A. Ellman, Tetrahedron 1997, 53, 6635-6644.
11. W. M. De Borggraeve, F. R. Rombouts, E. V. Van der Eycken, S. M. Toppet, G. J. Hoornaert, Tetrahedron Lett. 2001, 42, 5693-5695.
12. [a] Tuftsin: C. V. Valdeavella, H. D. Blatt, B. M. Pettitt, Int. J. Pept. Protein Res. 1995, 46, 372-380.
13. [b] Decorin/DS-PGII: Y. J. Wang, P. G. Scott, J. Sejbal, G. Kotovych, Can. J. Chem. 1996, 74, 389-401.
14. [c] Somatostatin: D. Gramberg, C. Weber, R. Beeli, J. Inglis, C. Bruns, J. A. Robinson, Helv. Chim. Acta 1995, 78, 1588-1606.
15. A. Jabs, M. S. Weiss, R. Hilgenfeld, J. Mol. Biol. 1999, 286, 291-304.
16. [a] D. S. Kemp, E. T. Sun, Tetrahedron Lett. 1982, 37, 3759-3760.
17. [b] J.-P. Dumas, J. P. Germanas, Tetrahedron Lett. 1994, 35, 1493-1496.
18. [c] J. A. Robinson, D. Gramberg, Tetrahedron Lett. 1994, 6, 861-864.
19. [d] K. Kyonghee, J. P. Germanas, J. Org. Chem. 1997, 62, 2847-2852.
20. [e] P. K. C. Paul, P. A. Burney, M. M. Campbell, D. J. Osguthorpe, Bioorg. Med. Chem. Lett. 1992, 2, 141-144.
21. [f] L. Halab, W. D. Lubell, J. Am. Chem. Soc. 1999, 64, 3312-3321.
22. [g] S. Derrer, J. E. Davies, A. B. Holmes, J. Chem. Soc., Perkin Trans. 1 2000, 2957-2967.
23. F. J. R. Rombouts, W. De Borggraeve, S. M. Toppet, F. Compernolle, G. J. Hoornaert, Tetrahedron Lett. 2001, 42, 7397-7399.
24. J. Vekemans, C. Pollers-Wieërs, G. Hoornaert, J. Heterocycl. Chem. 1983, 20, 919-923.
25. K. J. Buysens, D. M. Vandenberghe, G. J. Hoornaert, Tetrahedron 1996, 52, 9161-9178.
26. This method is misleadingly called a Monte Carlo conformer search. Monte Carlo simulations also generate structures by random displacements, but do not minimize the resulting structures. Instead, energies are calculated immediately and are used to obtain thermodynamic properties.
27. Feature implemented in Macromodel, based on: C. A. G Haasnoot, F. A. A. M. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792.
28. Except for 26, which can be viewed as a bridged Gly-Gly dipeptide, the bridged cis-amide mimics 1, 2 and 27 shown in Figure 5 are the enantiomeric forms corresponding to the natural L-amino acids after omission of the bridging elements.
29. J. B. Ball, P. F. Alewood, J Mol. Recognit. 1990, 3, 55-64.
30. J. B. Ball, R. A. Hughes, P. F. Alewood, P. R. Andrews, Tetrahedron 1993, 49, 3467-3478.
31. G. Müller, G. Hessler, H. Y. Decornez, Angew. Chem. Int. Ed. 2000, 39, 894-896.
32. P. N. Lewis, F. A. Momany, H. A. Scheraga, Biochim. Biophys. Acta 1973, 303, 211-229.
33. F. J. R. Rombouts, D. A. J. Vanraes, J. Wynendaele, P. K. Loosen, I. Luyten, S. Toppet, F. Compernolle, G. J. Hoornaert, Tetrahedron 2001, 57, 3209-3220.
34. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
35. [a] S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Ghio, G. Algona, S. Profeta, Jr., P. J. Weiner, J. Am. Chem. Soc. 1984, 106, 765-784.
36. [b] S. J. Weiner, P. A. Kollman, D. T. Nguyen, D. A. Case, J. Comput. Chem. 1986, 7, 230-252.
37. W. C. Still, A. Tempczyk, R. C. Hawley, T. Hendrickson, J. Am. Chem. Soc 1990, 112, 6127-6129.
38. [a] G. Chang, W. C. Guida, W. C. Still, J. Am. Chem. Soc. 1989, 111, 4379-4386.
39. [b] M. Saunders, K. N. Houk, Y.-D. Wu, W. C. Still, M. Lipton, G. Chang, W. C. Guida, J. Am. Chem. Soc. 1990, 112, 1419-1427.
40. S. Miertus, E. Scrocco, J. Tomasi, J. Chem. Phys. 1981, 55, 117-129.
41. A. Klamt, G. Schuurmann, J. Chem. Soc., Perkin Trans. 2 1993, 799-805.
42. A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235.
43. A. Klamt, V. Jonas, T. Bürger, J. C. W. Lohrenz, J. Phys. Chem. A 1998, 102, 5074-5085.
44. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Milliam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98 (Revision A.5), Gaussian Inc., Pittsburgh, PA, 1998.
45. W. D. Cornell, P. Cieplak, C. I. Bayly, I. R. Gould, K. M. Merz, Jr., D. M. Ferguson, D. C. Spellmeyer, T Fox, J. W. Caldwell, P. A. Kollman, J. Am. Chem. Soc. 1995, 117, 5179-5197.
46. W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, R. W. Impey, M. L. Klein, J. Chem. Phys. 1983, 79, 926-935.
47. 13C NMR spectra were taken at 50 °C, after addition of a drop of DCl.
48. Resolution-enhancing Lorentz-Gauss function applied to FID: lb: -2.0 Hz; gb: 0.5 Hz.
49. W. R. Bowman, P. T. Stephenson, N. K. Terret, A. R. Young, Tetrahedron 1995, 51, 7959-7980.
50. T. Inaba, M. Fujita, K. Ogura, J. Org. Chem. 1991, 56, 1274-1279.