Spectroscopic study and PM5 semiempirical calculations of tautomeric forms of gossypol Schiff base with n-butylamine in the solid state and in the solution

Journal of Molecular Structure

Volumn 646, Issue 1-3, 2003, Pages 161-168

  Przybylski, Piotr ^a   Wojciechowski, Grzegorz ^a   Schilf, Wojciech ^b   Brzezinski, Bogumil ^a   Bartl, Franz ^c  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^c CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

13C NMR; 15N NMR; 1H NMR; COSY; CP MAS; FT IR; Gossypol; Gossypol Schiff base; HETCOR; N Butylamine; PM5 calculation

Indexed keywords

BUTYLAMINE; ENAMINE; GOSSYPOL; GOSSYPOL SCHIFF BASE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CRYSTAL STRUCTURE; DRUG STRUCTURE; GEOMETRY; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; SOLID STATE; SPECTROPHOTOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037453991     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(02)00621-X     Document Type: Article

References (47)

1. R. Adams, R.C. Morris, T.A. Geissman, D.J. Butterbaugh, K.C. Kirkpatrick, J. Am. Chem. Soc. 60 (1938) 2193.
2. T.J. King, L.B. de Silva, Tetrahedron Lett. 3 (1968) 261.
3. Q.B. Cass, E. Tiritan, S.A. Matlin, E.C. Freire, Phytochemistry 30 (1991) 2655.
4. F.E. Carruth, J. Biol. Chem. 32 (1917) 87.
5. R. Adams, T.A. Geissman, J.D. Edwards, Chem. Rev. 60 (1960) 555.
6. D.K. Zheng, Y.K. Si, J.K. Meng, J. Zhou, L. Huang, J. Chem. Soc., Chem. Commun. (1985) 168.
7. D.S. Sampath, P. Balaram, J. Chem. Soc., Chem. Commun. (1986) 649.
8. S.A. Matlin, R. Zhou, G. Bialy, R.P. Blye, R.H. Naqvi, M.C. Lindberg, Contraception 31 (1985) 141.
9. R.C. Stein, A.F.A. Joseph, S.A. Matlin, D.C. Cunningham, H.T. Ford, C.R. Coombes, Cancer Chem. Pharmacol. 30 (1992) 480.
10. E.N. Gilbert, J.E. O'Reilly, C.J.G. Chang, Y.C. Lin, R.W. Brueggemeier, Life Sci. 57 (1995) 61.
11. A.G. Medentsev, V.K. Akimenko, Microbiology 68 (1999) 10.
12. D.L. Vander Jagt, L.M. Deck, R.E. Royer, Curr. Med. Chem. 7 (2000) 479.
13. G.P. Tuszynski, G. Cossu, Cancer Res. 44 (1984) 768.
14. P.J.E. Quintana, A. de Peyster, S. Klatzke, H.J. Park, Toxicol. Lett. 117 (2000) 85.
15. National Coordinating group on Male Fertility, Chin. Med. 4 (1978) 471.
16. M. Chang, Z. Gu, S. Saksena, Contraception 21 (1980) 461.
17. S. Segal, Gossypol, A Potential Contraceptive for Men, Plenum Press, New York, 1985.
18. B. Polsky, S.J. Segal, P.A. Baron, J.W.M. Gold, H. Ueno, D. Armstrong, Contraception 39 (1989) 579.
19. E.M. Couthino, C. Athayde, G. Atta, Z.P. Gu, Z.W. Chen, G.W. Sang, E. Emuveyan, A.O. Adekunle, J. Mati, J. Otubu, M.M. Reidenberg, S.J. Segal, Contraception 61 (2000) 61.
20. M.D. Shelley, L. Hartley, R.G. Fish, P. Groundwater, J.J.G. Morgan, D. Mort, M. Mason, A. Evans, Cancer Lett. 135 (1999) 171.
21. R.E. Royer, L.M. Deck, T.J. Vander Jagt, F.J. Martinez, R.G. Mills, S.A. Young, D.L. Vander Jagt, J. Med. Chem. 38 (1995) 2427.
22. M.R. Flack, R.G. Pyle, N.M. Mullen, B. Lorenzo, Y.W. Wu, R.A. Knazek, B.C. Nusule, M.M. Reidenberg, J. Clin. Endocrinol. Metab. 76 (1993) 1019.
23. R. Baumgrass, M. Weiwad, F. Erdmann, J. Biol. Chem. 276 (2001) 47914.
24. P.J.E. Quintana, A. de Peyster, S. Klatzke, H.J. Park, Toxicol. Lett. 117 (2000) 85.
25. A.S.H. Li, B. Bandy, S.S. Tsang, A.J. Davidson, Free Radical Res. 33 (2000) 551.
26. V. Razakantoanina, N.K.P. Phung, G. Jaureguiberry, Parasitol. Res. 86 (2000) 665.
27. K.J. Lee, K. Dabrowski, J. Agric. Food Chem. (2001).
28. M.D. Shelley, L. Hartley, P.W. Groundwater, R.G. Fish, Anti-Cancer Drugs 11 (2000) 209.
29. R.G. Fish, P.W. Groundwater, J.J.G. Morgan, Tetrahedron: Asymmetry 6 (1995) 873.
30. P. Przybylski, B. Brzezinski, Biopolymers (Biospectroscopy) 67 (2001) 61.
31. S.A. Matlin, S. Roshdy, Q.B. Cass, L.C.G. Freitas, R.L. Longo, I. Malvestiti, J. Braz. Chem. Soc. 1 (1990) 128.
32. P. Przybylski, B. Brzezinski, F. Bartl, Biopolymers (Biospectroscopy) 65 (2002) 111.
33. B. Brzezinski, J. Olejnik, S. Paszyc, J. Mol. Struct. 239 (1990) 23.
34. B. Brzezinski, S. Paszyc, G. Zundel, Chem. Phys. Lett. 167 (1990) 7.
35. B. Marciniak, G. Schroeder, H. Kozubek, B. Brzezinski, J. Chem. Soc. Perkin Trans. 2 (1991) 1359.
36. B. Brzezinski, B. Marciniak, S. Paszyc, J. Mol. Struct. 268 (1992) 61.
37. P. Przybylski, G. Wojciechowski, B. Brzezinski, H. Kozubek, B. Marciniak, S. Paszyc, J. Mol. Struct. 569 (2001) 147.
38. P. Przybylski, K. Jasiński, B. Brzezinski, F. Bartl, J. Mol. Struct. 611 (2002) 193.
39. J.J.P. Stewart, Meth. J. Comput. Chem. 10 (1989) 209.
40. J.J.P. Stewart, J. Comput. Chem. 12 (1991) 320.
41. B. Brzezinski, G. Zundel, Chem. Phys. Lett. 75 (1980) 500.
42. B. Brzezinski, G. Zundel, J. Chem. Phys. 86 (1982) 5135.
43. G. Zundel, A. Mueller, H. Ratajczak, D.W.E Junge, (Eds.), Electron and Proton Transfer in Chemistry and Biology, Elsevier, Amsterdam, 1992, p. 313.
44. B. Brycki, B. Brzezinski, B. Marciniak, S. Paszyc, Spectrosc. Lett. 24 (1991) 509.
45. B. Kamienski, W. Schilf, T. Dziembowska, Z. Rozwadowski, A. Szady-Chelmieniecka, Solid State NMR 16 (2000) 285.
46. W. Schilf, B. Kamienski, T. Dziembowska, J. Mol. Struct. 602 (2002) 41.
47. W. Schilf, A. Szady-Chelmieniecka, E. Grech, P. Przybylski, B. Brzezinski, J. Mol. Struct. 643 (2002) 115.