An ab initio study of a model compound of penicillins

Journal of Molecular Structure: THEOCHEM

Volumn 491, Issue 1-3, 1999, Pages 177-185

  Pena Gallego A ^a   Cabaleiro Lago, E M ^a   Fernandez Ramos A ^a   Hermida Ramon J M ^a   Martinez Nunez E ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Ab initio calculations; Conformational analysis; Penicillins; Pseudorotation process; Lactams

Indexed keywords

PENICILLIN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; ENERGY; MOLECULAR MODEL; MOLECULAR STABILITY; OPTICAL ROTATION; STRUCTURE ACTIVITY RELATION;

EID: 0037675368     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(99)00108-6     Document Type: Article

References (35)

1. D.B. Boyd, Theoretical and physicochemical studies on β-lactam antibiotics, in: R.B. Morin, H. German (Eds.), Chemistry and Biology of β-Lactam Antibiotics, 1, Academic Press, New York, 1982, p. 437.
2. W. Lwowski, in: A.R. Katritzky, C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry, 7, Pergamon, Oxford, 1984, Part 5.
3. A. Padwa, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry, 1B, Pergamon, Oxford, 1996, Part 1.20.
4. M.I. Page, The Chemistry of β-Lactams, Chapman and Hall, New York, 1992.
5. J.M. Ghuysen, J.M. Frère, M. Leygh-Bouille, J. Coyette, J. Dusart, M. Nguyen-Disteche, Annu. Rev. Biochem. 48 (1979) 73.
6. M. Gorman, C.W. Ryan, in: E.H. Flynn (Ed.), Cephalosporins and Penicillins: Chemistry and Biology, Academic Press, New York, 1972, p. 532.
7. D.B. Boyd, R.B. Hermann, D.E. Presti, M.M. Marsh, J. Med. Chem. 18 (1975) 408.
8. K.E. Price, in: D. Perlman (Ed.), Structure-Activity Relationship among the Semisynthetic Antibiotics, Academic Press, New York, 1977, p. 1.
9. J.R. Johnson, R.B. Woodward, R. Robinson, in: D. Crowfoot, C.W. Bunn, B.W. Rogers-Low, A. Turner-Jones (Eds.), The Chemistry of Penicillin, Princeton University Press, Princeton, 1949, p. 440.
10. N.V. Joshi, R. Virudachalam, V.S.R. Rao, Curr. Sci. 47 (1978) 933.
11. N.V. Joshi, V.S.R. Rao, J. Biosci. 4 (1982) 209.
12. N.C. Cohen, J. Med. Chem. 26 (1983) 259.
13. C.M. Dobson, L.O. Ford, S.E. Summers, R.J.P. Williams, J. Chem. Soc. Faraday Trans. II 71 (1975) 1145.
14. R.J.P. Williams, Angew. Chem. Int. Ed. 16 (1977) 766.
15. M. Yoshimoto, S. Ishihara, E. Nakayama, N. Soma, Tetrahedron Lett. (1972) 2923.
16. D.D. Dexter, J.M.v.d. Veen, J. Chem. Soc., Perkin Trans. 1 1 (1978) 185.
17. M.A. Palafox, J.L. Núñez, M. Gil, J. Phys. Chem. 99 (1995) 1124.
18. B. Fernández, L. Carballeira, M.A. Ríos, Biopolymers 32 (1992) 97.
19. J. Frau, M. Coll, J. Donoso, F. Muñoz, F.G. Blanco, J. Mol. Struct. (Theochem) 231 (1991) 109.
20. J. Frau, J. Donoso, F. Muñoz, F.G. Blanco, J. Mol. Struct. (Theochem) 251 (1991) 205.
21. J. Frau, J. Donoso, F. Muñoz, F.G. Blanco, J. Comp. Chem. 6 (1992) 681.
22. J. Frau, J. Donoso, B. Vilanova, F. Muñoz, F. García-Blanco, Theor. Chim. Acta 86 (1993) 229.
23. J. Frau, J. Donoso, F. Muñoz, F.G. Blanco, J. Comp. Chem. 14 (1993) 1545.
24. J. Frau, J. Donoso, F. Muñoz, F. García-Blanco, Helv. Chim. Acta 77 (1994) 1557.
25. J. Frau, J. Donoso, F. Muñoz, F. García-Blanco, Helv. Chim. Acta 79 (1996) 353.
26. M. Coll, J. Frau, J. Donoso, F. Muñoz, J. Mol. Struct. (Theochem) 426 (1998) 323.
27. J. Pitarch, M.F. Ruiz-López, E. Silla, J.L. Pascual-Ahuir, I. Tuñón, J. Am. Chem. Soc. 120 (1998) 2146.
28. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Peterson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian 94, Revision E.2; Gaussian, Inc., Pittsburgh, PA, 1995.
29. C.C. Roothan, J. Rev. Mod. Phys. 23 (1951) 69.
30. C. Møller, M.S. Plesset, Phys. Rev. 46 (1934) 618.
31. R.G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989.
32. A.D. Becke, Phys. Rev. A 38 (1988) 3098.
33. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1986) 785.
34. R. Krishnan, J.A. Pople, Int, J. Quant. Chem. 14 (1978) 91.
35. A. Balsamo, P. Domiano, F. Macchia, M. Nardelli, Eur. J. Med. Chem., Chim. Ther. 15 (1980) 559.