NMR Studies of Ca2+ Complexes of Annonaceous Acetogenins

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4811-4815

  Peyrat, Jean François ^a   Mahuteau, Jacqueline ^a   Figadère, Bruno ^a   Cavé, André ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ANNONACIN; CALCIUM; SQUAMOCIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYTOTOXICITY; KINETICS; MEMBRANE TRANSPORT; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0030832570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962031b     Document Type: Article

References (16)

1. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. Recent advances in the acetogenins of Annonaceae. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202.
2. Cavé, A.; Cortes, D.; Figadère, B.; Laurens, A. In Progress in the Chemistry of Organic Natural Products', Hertz, W., Eds.; Springer-Verlag; Wien, New York, 1997; Vol. 70, pp 81-288.
3. Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 and references cited therein.
4. Figadère, B.; Cavé, A. Studies in Natural Products Chemistry. In Stereoselective Synthesis; Atta-ur-Raman, Eds.; Elsevier; Amsterdam, 1996; Vol. 18, pp 193-227.
5. Saaaki, S.; Maruta, K.; Naito, H.; Sugihara, H.; Hiratani, K.; Maeda, M. Tetrahedron Lett. 1995, 36, 5571-5574.
6. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167.
7. Friederich, T.; van Heek, P.; Leif, H.; Ohnishi, T.; Forche, E.; Kunze, B.; Jansen, R.; Trowitzsch-Kienast, W.; Höfle, G.; Reichenbach, H.; Weiss, H. Eur. J. Biochem. 1994, 219, 691-698.
8. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348.
9. Araya, H.; Fujimoto, Y.; Hirayama, K. J. Syn. Org. Chem. Jpn. 1994, 52, 765-777.
10. Peyrat, J.-F.; Figadère, B.; Cavé, A.; Mahuteau, J. Tetrahedron Lett. 1995, 36, 7653-7656.
11. Still, W. C.; Hauck, P.; Kempf, D. Tetrahedron Lett. 1987, 28, 2817-2820.
12. See, for instance: Echegoyen, L.; Kaifer, A.; Durst, H.; Schultz, R. A.; Dishong, D. M.; Goli, D. M.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 5100-5103 and references cited therein.
13. Compounds with amide functions have been shown to complex bivalent ions such as calcium; see, for instance: Raban, M.; Burch, D. L.; Hortelano, E. R.; Durocher, D. J. Org. Chem. 1994, 59, 1283-1287.
14. Berstein, F. C.; Koetzle, T. F.; Williams, G. J. B.; Meyer, E. F., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, M. J. Mol. Biol. 1977, 112, 535-542.
15. -2.
16. Yu, J.-G.; Hu, X. E.; Ho, D. K.; Bean, M. F.; Stephens, R. E.; Cassady, J. M.; Brinen, L. S.; Clardy, J. J. Org. Chem. 1994, 59, 1598-1599.