Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins

Tetrahedron

Volumn 54, Issue 11, 1998, Pages 2401-2410

  Sasaki, Shigeki ^a   Maruta, Katsunori ^a   Naito, Hiroyuki ^a   Maemura, Rie ^a   Kawahara, Eiji ^a   Maeda, Minoru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; CALCIUM ION; LIGAND; MAGNESIUM ION; METAL ION; NATURAL PRODUCT; TETRAHYDROFURAN;

ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG POTENCY; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032510264     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10439-2     Document Type: Article

References (22)

1. 1. Reviews; a) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z. M.; He, K.; McLaughlin, J. L. Natural Product Reports 1996, 13, 275-306.
2. b) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447-1464,
3. c) Koert, U. ibid 1995, 115-132,
4. d) Fang, X.-P.; Rieser. M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27,
5. e) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-477.
6. 2. Hui, Y.-H.; Rupprecht, J. K.; Liu, Y. M.; Anderson, J. E.; Smith, D. L.; Chang, C.-J.; McLaughlin, J. L. ibid 1989, 52, 463-477.
7. 3. a) He, K.; Zeng, L.; Ye, Q.; Shi, G.E.; Oberlies, N.H.; Zhao, G.X.; Njoku, J. Mclaughlin, J. L. Pesticide Sci. 1997, 49, 372-378,
8. b) Landolt, J. L.; Ahammadsahib, K. L.; Hollingworth, R. M.; Barr, R.; Crane, F. L; Buerck, N. L.; Mccabe, G. P.; McLaughlin, J. L. Chemico-Biological Interactions 1995, 98, 1-13,
9. c) Morre, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-8.
10. 4. Araya, H.; Fujimoto, Y.; Hirayama, K. J. Syn. Org. Chem. Jpn. 1994, 52, 765.
11. 5. Li, G.; Still, W. C. Tetrahedron Lett. 1993, 34, 919-2.
12. 6. Schultz, W. J.; Etter, M. C.; Pocius, A. V.; Smith, S. J. Am. Chem. Soc. 1980, 102, 7981-82
13. 7. Anunann, D.; Guggi, M.; Pretsch, E.; Simon, W. Anal. Lett. 1975, 8, 709.
14. 8. a) Sasaki, S.; Naito, H.; Maruta, K.; Kawahara, E.; Maeda, M. Tetrahedron Lett. 1994, 35, 3337-40,
15. b) Sasaki, S.; Maruta, K.; Naito, H.; Sugihara, H.; Hiratani, K.; Maeda, M. ibid 1995, 36, 5571-4.
16. 9. Peyrat, J.-P.; Mahuteau, J.; Figadère, B.; Cavé, A., J. Org. Chem. 1997, 62, 4811-4815.
17. 10. a) Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. J. Org. Chem. 1995, 60, 4419-27,
18. b) Sasaki, S.; Maruta, K.; Naito, H.; Maemura, R.; Kawahara, E.; Maeda, M. Chem. Pharm. Bull, in press.
19. 11. Wilcox, C. S.; Cowart, M. D. Tetrahedron Lett. 1986, 27, 5563-6.
20. 12. Deber, C. M.; Pfeiffer, D. R. Biochemistry 1976, 15, 132-141.
21. 13. Lehn, J. -M. Structure and Bonding vol 16: Springer-Verlag, 1973, pp 1.
22. 14. The stable complex structures were initially searched by MD with augmented MM2 parameters, and further optimized by MOPAC or ZINDO. Calculations were performed with CAChe-Group Server (IBM RS6000) system on Macintosh.