Conformational complexity in seven-membered cyclic triazepinone/open hydrazones. 2. Molecular modeling and X-ray study

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 5089-5095

  Simeonov, Mario F ^a,b   Fülöp, Ferenc ^a,c   Sillanpää, Reijo ^a   Pihlaja, Kalevi ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^c UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 BENZOTRIAZEPINE DERIVATIVE; HYDRAZONE DERIVATIVE;

ARTICLE; DRUG CONFORMATION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PSYCHOPHARMACOLOGY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0030742342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962323c     Document Type: Article

References (39)

1. (a) St-Jacques, M.; Vaziri, C. Can. J. Chem. 1973, 51, 1192.
2. (b) Allinger, N. L.; Sprague, J. T. J. Am. Chem. Soc. 1972, 94, 5734.
3. (c) Kabuss, S.; Schmid, H. G.; Friebolin, H.; Faisst, W. Org. Magn. Reson. 1970, 2, 19.
4. (d) Hendrickson, J. B. J. Am. Chem. Soc. 1961, 83, 4537.
5. (e) Ermer, O.; Lifson, S. J. Am. Chem. Soc. 1973, 95, 4121.
6. (f) Zuccarello, F.; Buemi, G.; Favini, G. J. Mol. Struct. 1973, 18, 295.
7. Kabuss, S.; Lüttringhaus, A.; Friebolin, H.; Schmid, H. G.; Merke, R. Tetrahedron Lett. 1966, 719.
8. (a) Wasylishen, R. E.; Rice, K. C.; Weiss, U. Can. J. Chem. 1975, 53, 414.
9. (b) Gál, M.; Pallagi, I.; Sohár, P.; Fülöp, F.; Kálmán, A. Tetrahedron 1989, 45, 3513.
10. (c) Aversa, M. C.; Giannetto, P.; Romeo, G.; Ficarra, P.; Vigorita, M. G. Org. Magn. Reson. 1981, 15, 394.
11. (d) Malik, F.; Hassan, M.; Rosenbaum, D.; Duddeck, H. Magn. Reson. Chem. 1989, 27, 391.
12. (a) Gilman, N. W.; Rosen, P.; Earley, J. V.; Cooke, C. M.; Todaro, L. J. J. Am. Chem. Soc. 1990, 112, 3969.
13. (b) Gilman, N. W.; Rosen, P.; Earley, J. V.; Cook, C. M.; Blount, J. F.; Todaro, L. J. J. Org. Chem. 1993, 58, 3285.
14. (c) Finner, E.; Zeugner, H.; Benson, W. Arch. Pharm. (Weinheim) 1989, 322, 507.
15. (d) Sanner, M. A.; Josef, K.; Johnson, R. E.; Dambra, Th.; Kowalczyk, P.; Kullnig, R. K.; Michaels, F. J. Org. Chem. 1993, 58, 6417.
16. (e) Katritzky, A. R.; Fan, W.-Q.; Greenhill, J. V.; Steel, P. J. J. Org. Chem. 1991, 56, 1299.
17. (a) Messinger, J.; Buss, V. J. Org. Chem. 1992, 57, 3320.
18. (b) Alkorta, I.; Villar, H. O.; Cachau, R. E.; J. Comput. Chem. 1993, 14, 571.
19. (c) Borea, P. A.; Dean, P. M.; Martin, I. L.; Perkins, T. D. Mol. Neuropharmacol. 1992, 2, 261.
20. (d) De Sarro, G. B.; Zappala, M.; Grasso, S.; Chimirri, A.; Spagnolo, C.; De Sarro, A. Mol. Neuropharmacol. 1992, 1, 195.
21. (a) For Part 1 see Pihlaja, K.; Simeonov, M. F.; Fülöp, F. J. Org. Chem. 1997, 62, 5080.
22. (b) Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
23. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899.
24. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
25. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221.
26. Robin, M. B.; Bovey, F. A.; Basch, H. The Chemistry of Amides; Zabinsky, J., Ed.; Interscience Publishers: London, 1970.
27. Kolossvary, I.; Guida, W. C. J. Am. Chem. Soc. 1993, 115, 2107.
28. Program PCMODEL/MMX, Serena Software, Bloomington, IN.
29. Jennings, W. B.; Worley, S. D. J. Chem. Soc., Perkin Trans. 2 1980, 1512.
30. Shvo, Y.; Nahlieli, A. Tetrahedron Lett. 1970, 4273.
31. Gajewski, J. J.; Gilbert, K.; McKelvie, J. Advances in Molecular Modelling; JAI Press: Greenwich, CT, 1990.
32. Burkert, U.; Allinger, N. L. Molecular Mechanics, ACS Monograph 177, American Chemical Society: Washington, DC, 1982.
33. Stewart, J. J. P. FJSRL TR-90-0004, 1990.
34. Tripos Associates, Inc., 1992.
35. Boyd, D. B.; Smith, D. W.; Stewart, J. J. P.; Wimmer, E. J. Comput. Chem. 1988, 9, 387.
36. Gilmore, C. J. J. Appl. Crystallogr. 1982, 17, 42.
37. (a) TEXSAN-TEXRAY: Single Crystal Structure Analysis Package, Version 5.0, Molecular Structure Corporation, The Woodlands, TX, 1989.
38. (b) Johnson, C. K. ORTEP-II, Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
39. The authors have deposited atomic coordinates for 1, 5, and 6 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.