Synthesis, NMR studies and conformational analysis of oxazolidine derivatives of the β-adrenoreceptor antagonists metoprolol, atenolol and timolol

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 1998, Pages 199-206

  Moloney, Gerard P ^a   Craik, David J ^b   Iskander, Magdy N ^a   Nero, Tracy L ^c  

^a MONASH UNIVERSITY   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038268405     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706442j     Document Type: Article

References (65)

1. M. A. Barrett, in Beta-adrenoceptive agonists; in Recent Advances in Cardiology, ed. Churchill Livingstone, Edinburgh, London, 1973, p. 289.
2. B. N. C. Pritchard, Am. Heart J., 1970, 79, 128.
3. B. N. C. Pritchard and P. M. S. Gillam, Brit. Med. J., 1969, 1, 7.
4. B. N. C. Pritchard, in Cardiovascular Drugs Vol. 2, β-Adrenoceptor blocking drugs, ed. G. S. Avery, ADIS Press, Seaforth, Australia, 1977, p. 85.
5. D. E. Jewitt and B. N. Singh, Prog. Cardiovasc. Dis., 1973, 16, 421.
6. B. N. Singh and D. E. Jewitt, Drugs, 1974, 7, 426.
7. J. Hamer and E. Sowton, Am. J. Cardiol., 1966, 18, 354.
8. H. Bundgaard, A. Buur, S. C. Chang and V. H. L. Lee, Int. J. Pharm., 1988, 46, 77.
9. H. Bundgaard, A. Buur, S. C. Chang and V. H. L. Lee, Int. J. Pharm., 1986, 33, 15.
10. S. J. Sorensen and S. R. Abel, The Annals of Pharmacotherapy, 1996, 30, 43.
11. Australian Pharmaceutical Formulary and Handbook, 13th edn., ed. R. A. Anderson, Griffin Press Ltd., Netley, South Australia, 1983, p. 371.
12. J. Alexander, R. Cargill, S. R. Michelson and H. Schwam, J. Med. Chem., 1988, 31, 318.
13. W. P. Munroe, J. P. Rindone and R. M. Kershner, Drug Intell. Clin. Pharm., 1985, 19, 85.
14. G. Alvan, B. Calissendorff, P. Seideman, K. Widmark and G. Widmark, Clin. Pharmacokin., 1980, 5, 95.
15. C. J. Schmitt, V. J. Lotti and J. C. Le Douarec, Arch. Opthamol., 1980, 98, 547.
16. V. J. Stella and K. J. Himmelstein, J. Med. Chem., 1980, 23, 1275.
17. N. Bordor and G. Visor, Exp. Eye. Res., 1984, 38, 621.
18. D. A. McClure, in Prodrugs as novel drug delivery systems, American Chemical Society, Washington, DC, 1975, p. 224.
19. A. Hussain and J. E. Truelove, J. Pharm. Sci., 1976, 65, 1510.
20. R. J. Lee, D. B. Evans and H. B. Sherrin, Eur. J. Pharmacol., 1975, 33, 371.
21. E. Duzman, C. C. Chen, J. Anderson, M. Blumenthal and H. Twizer, Arch. Opthalmol., 1982, 100, 1916.
22. L. Z. Bito, Exp. Eye. Res., 1984, 38, 181.
23. H. Bundgaard, E. Falch, C. Larsen, G. C. Mosher and T. Mikkelson, J. Med. Chem., 1985, 28, 979.
24. A. Monge, I. Aldana, H. Cerecetto and A. Rivero, J. Heterocycl. Chem., 1995, 32, 1429.
25. H. Bundgaard and M. Johansen, Int. J. Pharm., 1982, 10, 165.
26. M. Johansen and H. Bundgaard, J. Pharm. Sci., 1983, 72, 1294.
27. G. P. Moloney, Synthesis and NMR studies of Oxazines and Oxazolidine based compounds, Ph.D. Thesis, Victorian College of Pharmacy Ltd., 1990.
28. A. Buur and H. Bundgaard, Int. J. Pharm., 1984, 18, 325.
29. J. A. Young-Harvey, I. D. Rae and I. H. Pitman, Int. J. Pharm., 1986, 30, 151.
30. H. Bundgaard and M. Johansen, J. Pharm. Sci., 1980, 69, 44.
31. D. Carlstiom, Acta Crystallogr., Sect. B, 1973, 29, 161.
32. M. Mathew and G. J. Palenik, J. Am. Chem. Soc., 1971, 93, 497.
33. Y. Barrans, M. Cotrait and J. Dangoumau, Acta Crystallogr., Sect. B, 1973, 29, 1264.
34. M. Gadret, M. Goursolle, J. M. Leger and J. C. Colleter, Acta Crystallogr., Sect. B, 1975, 31, 2780.
35. M. Gadret, M. Goursolle, J. M. Leger and J. C. Colleter, Acta Crystallogr., Sect. B, 1976, 22, 17.
36. P. N. Patil, D. D. Miller and U. Trendelenburg, Pharmacol. Rev., 1974, 26, 323.
37. J. M. George, L. B. Kier and J. R. Hoyland. Mol. Pharmacol., 1971, 7, 328.
38. A. M. Kuliev, B. R. Gasanov, E. A. Agaeva and S. B. Bilalov, Zh. Prikl. Spektrosk., 1973, 19, 506.
39. N. el Tayar, P. A. Carrupt, H. Van de Waterbeemd and B. Testa, J. Med. Chem., 1988, 31, 2072.
40. M. R. Linschoten, T. Bultsma, A. P. Ijzerman and H. Timmerman, J. Med. Chem., 1986, 29, 278.
41. M. Donne-Op den Kelder, T. Bultsma, H. Timmerman and B. Rademaker, J. Med. Chem., 1988, 31, 1069.
42. J. Dangoumau, Y. Barrans and M. Cotrait, J. Pharmacol., 1973, 4, 5.
43. H. A. Germer, J. Pharm. Pharmacol., 1974, 26, 799.
44. J. P. Beale, Cryst. Struct. Commun., 1972, 1, 67.
45. A. M. Anderson, Acta Chem. Scand., 1975, 29, 871.
46. R. R. Ison, P. Partington and G. C. K. Roberts, Mol. Pharmacol., 1973, 9, 756.
47. J. E. Forrest, R. A. Heacock and T. P. Forrest, J. Pharm. Pharmacol., 1970, 22, 512.
48. A. Balsamo, G. Ceccarelli, P. Crotti, B. Macchia, F. Macchia and P. Tognetti, Eur. J. Med. Chem., 1982, 17, 471.
49. P. S. Portoghese, J. Med. Chem., 1967, 10, 1057.
50. C. Romers, C. Altona, H. R. Buys and E. Havinga, Top. Stereochem., 1969, 4, 39.
51. A. Makriyannis, F. Sullivan and H. G. Mantner, Proc. Natl. Acad. Sci., 1972, 69, 3416.
52. J. Zaagsma, J. Med. Chem., 1979, 22, 441.
53. V. M. Kulkarni, N. Vasanthkumar, A. Saran and G. Govil, Int. J. Quant. Chem. Biol. Symp., 1979, 6, 153.
54. T. L. Nero, W. J. Louis and D. Iakovidis, J. Mol. Struct. (THEOCHEM.), 1993, 285, 251.
55. T. Jen and C. Kaiser, J. Med. Chem., 1977, 20, 693.
56. V. M. Kulkarni and E. Countinho, Int. J. Chem., 1991, 30B, 52.
57. A. Saran, S. Srivastava, V. M. Kulkarni and E. Coutinho, J. Mol. Struct., 1993, 279, 281.
58. R. Clarkson, ACS Symp. Ser., 1976, 27, 1.
59. SYBYL 6.2 molecular modelling package. Tripos Associates, St. Louis, MO, USA 63144.
60. M. Clark, R. D. Cramer and N. Van Opdenbosch, J. Comput. Chem., 1989, 10, 982.
61. J. Gasteiger and M. Marsili, Tetrahedron, 1980, 36, 3219.
62. W. P. Purcell and J. A. Singer, J. Chem. Eng. Data, 1967, 12, 235.
63. M. J. D. Powell, Math. Programm., 1977, 12, 241.
64. M. Lipton and W. C. Still, J. Camput. Chem., 1988, 9, 343.
65. M. Karplus, J. Am. Chem. Soc., 1963, 85, 2870.