Role of strong intramolecular N-H⋯N hydrogen bonds in determining the conformation of adenosine-receptor antagonists

Acta Crystallographica Section B: Structural Science

Volumn 62, Issue 4, 2006, Pages 634-641

  Ferretti, Valeria ^a   Pretto, Loretta ^a   Tabrizi, Mojgan Aghazadeh ^a   Gilli, Paola ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; DERIVATIVES; HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL);

ADENOSINE ANTAGONISTS; ADENOSINE RECEPTORS; PLANAR CONFORMATION; PYRAZOLO-TRIAZOLO-PYRIMIDINE DERIVATIVES;

MOLECULAR DYNAMICS;

ADENOSINE RECEPTOR; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRAZOLES; PYRIMIDINES; RECEPTORS, PURINERGIC P1; TRIAZOLES;

EID: 33746057525     PISSN: 01087681     EISSN: 01087681     Source Type: Journal    
DOI: 10.1107/S0108768106013966     Document Type: Article

References (49)

1. Accelrys Inc. (2003). MaterialStudio, MS modeling Version 3.0. Accelrys Inc., 6985 Scranton Road, San Diego, CA 92121-3752, USA.
2. Allen, F. H., Bellard, S., Brice, M. D., Cartwright, B. A., Doubleday, A., Higgs, H., Hummelink, T., Hummelink-Peters, B. G., Kennard, O., Motherwell, W. D. S., Rodgers, J. & Watson, D. G. (1979). Acta Cryst. B35, 2331-2339.
3. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-121.
4. Baraldi, P. G., Cacciari, B., Borea, P. A., Varani, K., Pastorin, G., de Ros, T., Tabrizi, M. A., Fruttarolo, F. & Spalluto, G. (2002). Curr. Pharm. Des. 6, 2299-2332.
5. Baraldi, P. G., Cacciari, B., Romagnoli, R., Spalluto, G., Moro, S., Klotz, K. N., Leung, E., Varani, K., Gessi, S., Merighi, S. & Borea, P. A. (2000). J. Med. Chem. 43, 4768-4780.
6. Baraldi, P. G., Tabrizi, M. A., Preti, D., Bovero, A., Fruttarolo, F., Romagnoli, R., El-Kashef, H., Moorman, A., Varani, K., Gessi, S., Merighi, S. & Borea, P. A. (2003). J. Med. Chem. 46, 1229-1241.
7. Baraldi, P. G., Tabrizi, M. A., Preti, D., Bovero, A., Fruttarolo, F., Romagnoli, R., Zaid, N. A, Moorman, A. R., Varani, K. & Borea, P. A. (2005). J. Med. Chem. 48, 5001-5008.
8. Baraldi, P. G., Tabrizi, M. A., Preti, D., Bovero, A., Romagnoli, R., Fruttarolo, F., Zaid, N. A., Moorman, A. R., Varani, K., Gessi, S., Meriggi, S. & Borea, P. A. (2004). J. Med. Chem. 6, 1434-1447.
9. Barone, V. & Adamo, C. (1996). J. Chem. Phys. 105, 11007-11019.
10. Berk, B., Akgun, H., Erol, K., Sirmagul, B., Gao, Z. G & Jacobson, K. A. (2006). Farmaco, 60, 974-980.
11. Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1997). J. Chem. Soc. Faraday Trans. pp. 945-952.
12. Bordwell, F. G., Bartmess, J. E. & Hautala, J. A. (1978). J. Org. Chem. 43, 3095-3101.
13. Bordwell, F. G. & Ji, G. Z. (1991). J. Am. Chem. Soc. 113, 8398-8401.
14. Buemi, G. & Zuccarello, F. (1996). J. Chem. Soc. Faraday Trans. 92, 347-351.
15. Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
16. Chung, G., Kwon, O. & Kwon, Y. J. (1997). J. Phys Chem. A, 101, 4628-4632.
17. Colotta, V., Catarzi, D., Varano, F., Cecchi, L., Filacchioni, G., Martini, C., Trincavelli, L. & Lucacchini, A. (2000). J. Med. Chem. 43, 3118-3124.
18. Curtiss, L. A. & Blander, M. (1988). Chem. Rev. 88, 827-841.
19. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
20. Ferretti, V., Bertolasi, V., Gilli, P. & Gilli, G. (1993). J. Phys. Chem. 97, 13568-13574.
21. Fossa, P., Pestarino, M., Menozzi, G., Mosti, L., Schenone, S., Ranize, A., Bondavilli, F., Trincavelli, M. L., Lucacchini, A. & Martini, C. (2005). Org. Biomol. Chem. 3, 2262-2270.
22. Fredholm, B. B., Ijzerman, A. P., Jacobson, K. A., Klotz, K.-N. & Linden, J. (2001). Pharm. Rev. 53, 527-552.
23. Frisch, M. J., Scheiner, A. C., Schaefer, H. F. III & Binkley, J. S. (1985). J. Chem. Phys. 82, 4194-4198.
24. Galabov, B., Ilieva, S., Hadjieva, B. & Dinchova, E. (2003). J. Phys. Chem. A, 107, 5854-5861.
25. Gao, Z.-G., Kim, S.-K., Biadatti, T., Chen, W., Lee, K., Barak, D., Kim, S. G., Johnson, C. R. & Jacobson, K. A. (2002). J. Med. Chem. 45, 4471-4484.
26. Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (1994). J. Am. Chem. Soc. 116, 909-915.
27. Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (2000). J. Am. Chem. Soc. 122, 10405-10417.
28. Gilli, P., Bertolasi, V., Pretto, L., Antonov, L. & Gilli, G. (2005). J. Am. Chem. Soc. 127, 4943-4953.
29. Gilli, P., Bertolasi, V., Pretto, L., Ferretti, V. & Gilli, G. (2004). J. Am. Chem Soc. 126, 3845-3855.
30. Gilli, P., Bertolasi, V., Pretto, L., Lycka, A. & Gilli, G. (2002). J. Am. Chem. Soc. 124, 13554-13567.
31. Gilli, P., Fernàndez-Castaño, C., Ferretti, V. & Gilli, G. (1996). XXVI Congress of the Italian Association of Crystallography, Alessandria, Italy, p. 124.
32. Gilli, P., Ferretti, V., Bertolasi, V. & Gilli, G. (1996). Advances in Molecule Structure Research, edited by M. Hargittai & I. Hargittai, pp. 67-102. Greenwich, Connecticut, USA: JAI Press Inc.
33. Hayallah, A. M., Sandoval-Ramirez, J., Reith, U., Schobert, U., Preiss, B., Schumacher, B., Daly, J. W. & Mueller, C. E. (2002). J. Med. Chem 45, 1500-1510.
34. Hess, S., Mueller, C. E., Frobenius, W., Reith, U., Klotz, K.-N. & Eger, K. (2000). J. Med. Chem. 43, 4636-4646.
35. Jacobson, K. A. (1998). Trends Pharmacol. Sci. 19, 184-191.
36. Jarvis, M. F. & Williams, M. (1987). Trends Pharmacol. Sci. 8, 330-332.
37. Kim, Y.-C., Ji, X., Melman, N., Linden, J. & Jacobson, K. A. (2000). J. Med. Chem. 43, 1165-1172.
38. Kim, Y.-C., de Zwart, M., Chang, L., Moro, S., von Frijtag Drabbe Kunzel, J., Melman, N., Ijzerman, A. P. & Jacobson, K. A. (1998). J. Med. Chem. 41, 2835-2845.
39. Kim, S., Marshall, M. A., Melman, N., Kim, H. S., Mueller, C. E., Linden, J. & Jacobson, K. A. (2002). J. Med. Chem. 45, 2131-2138.
40. Kobko, N., Paraskevas, L., del Rio, E. & Dannenberg, J. J. (2001). J. Am. Chem. Soc. 123, 4348-4349.
41. Maskill, H. (1985). The Physical Basis of Organic Chemistry. New York: Oxford University Press.
42. Müller, C. E. (1997). Exp. Opin. Ther. Patents, 5, 419-440.
43. Nardelli, M. (1995). J. Appl. Cryst. 28, 659-659.
44. Nonius (1997). Kappa-CCD Server Software. Nonius BV, Delft, The Netherlands.
45. Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307-326.
46. Perdew, J. P. & Wang, Y. (1992). Phys. Rev. B, 45, 13244-13249.
47. Richardson, P. J., Kase, H. & Jenner, P. G. (1997). Trends Pharmacol. Sci 18, 338-344.
48. Sheldrick, G. M. (1997). SHELX97. University of Göttingen, Germany.
49. Smith, M. B. & March, S. (2001). Advanced Organic Chemistry, 5th Ed. New York: J. Wiley and Sons.