Pyrroloisoquinoline-based tetrapeptide analogues mimicking reverse-turn secondary structures

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9765-9768

  Landoni, Nicola ^a   Lesma, Giordano ^a   Sacchetti, Alessandro ^a   Silvani, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GEOMETRY; INFRARED RADIATION; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE;

DIASTEREOISOMER; PYRROLOISOQUINOLINE; SECONDARY STRUCTURES; TETRAPEPTIDE ANALOGUES;

ORGANIC COMPOUNDS;

ISOQUINOLINE DERIVATIVE; PYRROLE DERIVATIVE; TETRAPEPTIDE;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; INFRARED SPECTROSCOPY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; PROTEIN PURIFICATION; PROTEIN SECONDARY STRUCTURE; STEREOCHEMISTRY;

ISOQUINOLINES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MONTE CARLO METHOD; OLIGOPEPTIDES; PROTEIN STRUCTURE, SECONDARY; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 36849034922     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701581j     Document Type: Article

References (38)

1. Lesma, G.; Meschini, E.; Recca, T.; Sacchetti, A.; Silvani, A. Tetrahedron 2007, 63, 5567-5578.
2. For review, see: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
3. Indolizidin-9-one amino acids: (a) Cluzeau, J.; Lubell, W. D. J. Org. Chem. 2004, 69, 1504-1512.
4. (b) Lamazzi, C.; Carbonnel, S.; Calinaud, P.; Troin, Y. Heterocycles 2003, 60, 1447-1456.
5. (c) Shimizu, M.; Nemoto, H.; Kakuda, H.; Takahata, H. Heterocycles 2003, 59, 245-255.
6. (d) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463-7471.
7. (e) De La Figuera, N.; Rosas, I.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. J. Chem. Soc., Chem. Commun. 1994, 613.
8. (a) Meldal, M.; Nielsen, T. E. J. Comb. Chem. 2005, 7, 599-610.
9. (b) Meldal, M.; Nielsen, T. E. Org. Lett. 2005, 7, 2695-2698.
10. (a) Grimes, J. H., Jr.; Angell, Y. M.; Kohn, W. D. Tetrahedron Lett. 2003, 44, 3835-3838.
11. (b) Andreu, D.; Ruiz, S.; Carreño, C.; Alsina, J.; Albericio, F.; Jeménez, M. A.; De la Figuera, N.; Herranz, R.; García- López, M. T.; González-Muñiz, R. J. Am. Chem. Soc. 1997, 119, 10579-10586.
12. (c) De la Figuera, N.; Alkorta, I.; García-López, M. T.; Herranz, R.; González-Muñiz, R. Tetrahedron 1995, 51, 7841-7856.
13. D'Alessio, S.; Gallina, C.; Gavuzzo, E.; Giordano, C.; Gorini, B.; Mazza, F.; Paglialunga Paradisi, M.; Panini, G.; Pochetti, G. Eur. J. Med. Chem. 2001, 36, 43-53.
14. (a) Martín-Martínez, M.; De la Figuera, N.; Latorre, M.; Herranz, R.; García-López, M. T.; Cenarruzabeitia, E.; Del Río, J.; González-Muñiz, R. J. Med. Chem. 2000, 43, 3770-3777.
15. (b) De la Figuera, N.; Martín-Martínez, M.; Herranz, R.; García-López, M. T.; Latorre, M.; Cenarruzabeitia, E.; del Río, J.; González-Muñiz, R. Bioorg. Med. Chem. Lett. 1999, 9, 43-48.
16. (a) Leach, A. R. Molecular Modelling: principles and applications; Prentice Hall: Upper Saddle River, NJ, 2001.
17. (a) Gellman, S. H.; Dado, G. P.; Liang, G.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173 and references cited therein.
18. (b) Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
19. (a) Vass, E.; Hollósi, M.; Besson, F.; Buchet, R. Chem. Rev. 2003, 103, 1917-1954.
20. (b) Gung, B. W.; Zhu, Z.; Zou, D.; Everingham, B.; Oyeamalu, A.; Crist, R. M.; Baudlier, J. J. Org. Chem. 1998, 63, 5750-5761.
21. (c) Boussard, G.; Marraud, M. J. Am. Chem. Soc. 1985, 107, 1825-1828.
22. Garrard, E. A.; Borman, E. C.; Cook, B. N.; Pike, E. J.; Alberg, D. G. Org. Lett. 2000, 23, 3639-3642.
23. In compound 7a, NOE contacts between H-1 and H-9b and between H-10 and H-9a were present, while for 7b NOE interaction of H-9a with both H-1 and H-10 were observed.
24. Spartan'06; Wavefunction, Inc.: Irvine, CA.
25. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467-3478.
26. (a) Van Rompaev, K.; Ballet, S.; Tömblöy, C.; De Wachter, R.; Vanommeslaeghe, K.; Biesemans, M.; Willem, R.; Tourwé, D. Eur. J. Org. Chem. 2006, 2899-2911.
27. (b) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569.
28. (c) Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
29. Hydrogen bonds are defined as non-bonded contacts between a nitrogen or oxygen and an hydrogen attached to nitrogen or oxygen, separated by a distance ranging from 1.6 to 2.1 Å and making an X-H-Y (X, Y = N, O) angle > 120°.
30. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
31. Rose, G. D.; Gierash, L. M.; Smith, J. A. Adv. Prot. Chem. 1985, 37, 1-109.
32. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R.; Tetrahedron 1993, 49, 3467-3478.
33. Scores are reported as obtained by the similarity analysis function implemented in the Spartan '06 software. The score is defined as [(1 - R2)/N], where R2 is the rms distance between template and molecule centers and N is the number of similarity centers.
34. Stevens, E. S.; Sugawara, N.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048-7050.
35. (a) Bittermann, H.; Böckler, F.; Einsiedel, J.; Gmeiner, P. Chem. Eur. J. 2006, 12, 6315-6322.
36. (b) Luppi, G.; Land, D.; Trigari, V.; Garavelli, M.; Garelli, A.; Tomasini, C. J. Org. Chem. 2003, 68, 1982-1993.
37. (c) Jones, I. G.; Jones, W.; North, M. J. Org. Chem. 1998, 63, 1505-1513.
38. Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389-400.