Jozimine A ('Dimeric' dioncophylline A), a non-natural michellamine analog with high antimalarial activity

Tetrahedron

Volumn 52, Issue 42, 1996, Pages 13409-13418

  Bringmann, Gerhard ^a   Saeb, Wael ^a   Koppler, Dagmar ^a   François, Guido ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b INSTITUTE OF TROPICAL MEDICINE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMODIONCOPHYLLINE A; ANTIMALARIAL AGENT; DIONCOPHYLLINE A; JOZIMINE A; MICHELLAMINE A; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; REACTION ANALYSIS;

ANIMALIA; PLASMODIUM FALCIPARUM; TRIPHYOPHYLLUM PELTATUM;

EID: 0030583517     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00812-5     Document Type: Article

References (35)

1. 1. "Acetogenic Isoquinoline Alkaloids", part 87; for part 86, see ref. 23. - "Antiprotozoal Activity of Naphthylisoquinoline Alkaloids", part 6; for part 5, see François, G.; Steenackers, T.; Timperman, G.; Aké Assi, L.; Haller, R. D.; Bär, S.; Isahakia, M. A.; Robertson, S. A.; Zhao, C.; De Souza, N. J.; Holenz, J. and Bringmann, G. Int. J. Parasitol., in press.
2. 2. (a) Bringmann, G.; Pokorny, F. in The Alkaloids; Cordell, G., Ed.; Academic Press: New York, Vol. 46, 1995, pp. 127-271. -
3. (b) Bringmann, G. Bull. Soc. Chim. Belg. 1996, in press.
4. 3. Bringmann, G.; Rübenacker, M.; Jansen, J. R.; Scheutzow, D.; Aké Assi, L. Tetrahedron Lett. 1990, 31, 639-642.
5. 4. Bringmann, G.; Jansen, J. R.; Reuscher H.; Rübenacker, M.; Peters, K.; von Schnering, H. G. Tetrahedron Lett. 1990, 31, 643-646.
6. 5. Bringmann, G.; Aké Assi, L; Rübenacker, M.; Ammermann, E.; Lorenz, G. German patent D. O. S. DE 4117080 A1, November 26, 1992; European Patent EP 0515856 A1, December 02, 1992.
7. 5. Bringmann, G.; Aké Assi, L; Rübenacker, M.; Ammermann, E.; Lorenz, G. German patent D. O. S. DE 4117080 A1, November 26, 1992; European Patent EP 0515856 A1, December 02, 1992.
8. 6. Bringmann, G.; Gramatzki, S.; Grimm, C.; Proksch, P. Phytochemistry 1992, 31, 3821-3825.
9. 7. François, G.; Bringmann, G.; Phillipson, J. D.; Aké Assi, L.; Dochez, C.; Rübenacker, M.; Schneider, C.; Wéry, M.; Warhurst, D. C.; Kirby, G. C. Phytochemistry 1994, 35, 1461-1464.
10. 8. François, G.; Bringmann, G.; Dochez, C.; Schneider, C.; Timperman, G.; Aké Assi, L. J. Ethnopharmacol. 1995, 46, 115-120.
11. 9. Manfredi, K. P.; Blunt, J. W.; Cardellina II, J. H.; McMahon, J. B.; Panell, L. L.; Cragg, G. M.; Boyd, M. R. J. Med. Chem. 1991, 34, 3402-3405.
12. 10. Boyd, M. R.; Hallock, Y. F.; Cardellina II, J. H.; Manfredi, K. P.; Blunt, J. W.; McMahon, J. B.; Buckheit, Jr., R. W.; Bringmann, G.; Schäffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740-1745.
13. 11. Cragg, G. M.; Boyd, M. R.; Cardellina II, J. H.; Newman, D. J.; Snader, K. M.; McCloud, T. G. Ethnobotany and the Search for New Drugs; Wiley, Chichester (Ciba Foundation Symposium 185), 1994; pp. 178-196.
14. 12. Hallock, Y. F.; Manfredi, K. P.; Blunt, J. W.; Cardellina II, J. H.; Schäffer, M.; Gulden, K. P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G.; Boyd, M. R. J. Org. Chem. 1994, 59, 6349-6355.
15. 13. Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Henschel, P.; Schäffer, M.; Stäblein, M.; Kelly, T. R.; Boyd, M. R. Heterocycles 1994, 39, 503-512
16. 14. Bringmann, G.; Harmsen, S.; Holenz, J.; Geuder, T.; Götz, R.; Keller, P. A.; Walter, R.; Hallock, Y. F.; Cardellina II, J. H.; Boyd, M. R. Tetrahedron 1994, 50, 9643-9648.
17. 15. Bringmann, G.; Götz, R.; Holenz, J.; Harmsen, S.; Walter, R. Liebigs Ann. Chem. 1996, in press.
18. 16. Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621-7624.
19. 17. Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. Tetrahedron Lett. 1994, 35, 8747-8750.
20. 18. Hobbs, P. D.; Upender, V.; Liu, J.; Pollart, D. J.; Thomas, D. W.; Dawson, M. I. J. Chem. Soc., Chem. Commun. 1996, 8, 923-924.
21. 19. Bringmann, G.; Zagst, R.; Reuscher, H.; Aké Assi, L. Phytochemistry 1992, 31, 4011-4014.
22. 20. Hallock, Y. F.; Hughes, C. B.; Cardellina II, J. H.; Schäffer, M.; Gulden, K. P.; Bringmann, G.; Boyd, M. R. Nat. Prod Lett. 1995, 6, 315-320.
23. 21. Berthelot, J.; Guette, C.; Desbéne, P. L.; Basselier, J. J.; Chaquin, P.; Masure, D. Can. J. Chem. 1989, 67, 2061-2066.
24. 22. Claisen, L.; Eisleb, O. Justus Liebigs Ann. Chem. 1913, 401, 21-119.
25. 23. Bringmann, G.; Saeb, W.; Peters, K.; Peters, E. M.; J. Chem. Soc., Chem. Commun., submitted.
26. 24. Wittig, G.; Klar, G. Justus Liebigs Ann. Chem. 1967, 704, 91-108.
27. 25. Although this dimeric dioncophylline A has as yet not been found in nature, it has been given a trivial name in order to avoid lenthy rational or half-rational nomenclature; this name is derived from the Kiswahili word 'jozi', meaning 'pair' or 'couple'.
28. 26. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355-360.
29. 27. Bringmann, G.; Koppler, D.; Scheutzow, D.; Porzel, A. Magn. Reson. Chem., submitted.
30. 28. Hallock, Y. F.; Cardellina II, J. H.; Boyd, M. R.; Saeb, W.; Bringmann, G., to be published.
31. 2/MeOH (9:1) as the eluent.
32. 30. Trager, W.; Jensen, J. B. Science 1976, 193, 673-675.
33. 31. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Antimicrob. Agents Chemother. 1979, 16, 710-718.
34. 32. François, G.; Timperman, G.; Holenz, J.; Aké Assi, L.; Geuder, T.; Maes, L.; Dubois, J.; Hanocq, M.; Bringmann, G. Ann. Trop. Med. Parasitol. 1996, 90, 115-123.
35. 33. Diem, K. in Scientific Tables; Sixth Edition; Documenta Geigy: Basel, 1962; pp. 54-55.