Synthesis of (±)-10,10-dimethylhuperzine A - A huperzine analogue possessing a slower enzyme off-rate

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 3, 1996, Pages 259-262

  Kozikowski, Alan P ^a   Ding, Qingjie ^a   Saxena, Ashima ^b   Doctor, Bhupendra P ^b  

^a GEORGETOWN UNIVERSITY   (United States)

^b WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10,10 DIMETHYLHUPERZINE A; ACETYLCHOLINESTERASE; HUPERZINE A; HUPERZINE A DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; COW; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; NONHUMAN; SERUM;

EID: 0030041404     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00012-1     Document Type: Article

References (22)

1. Relman, A. S. N. Eng. J. Med. 1991, 324, 349.
2. Whitehouse, P. J.; Price, D. L.; Struble, R G.; Clark, A. W.; Coyle, J. T.; DeLong, M. R. Science 1992, 215, 1237;
3. Wilcock, G. K.; Esiri, M. M.; Bowen, D. M.; Smith, C. C. T. Neuropath. Appl. Neurobiol., 1983, 9, 175:
4. Hallack, M.; Giacobini, E. Neuropharmacology 1989, 28, 199;
5. John, V.; Lieberburg, I.; Thorsett, E. D. Alzheimer's Disease: Current Therapeutic Approaches. Ann. Rep. Med. Chem. 1993, 28, 197.
6. Liu, J. S. et al. Can. J. Chem. 1986, 64, 837;
7. Ayer, W. A.; Kasitu, G. C. Can. J. Chem. 1989, 67, 1077;
8. Ayer, W. A. et al. Can. J. Chem. 1989, 67, 1538.
9. Zhang, R. W.; Tang, X. C.: Man, Y. Y.; Sang, G. W.; Zhang, Y. D.; Ma, X. X.; Zhang, C. L.; Yang, R. M. Acta Pharmacol. Sin. 1991, 12, 250;
10. Yu, C.-M. et al, US Patent 5, 177, 082, Jan. 1993.
11. Zhu. X. D.; Giacobini, E. J. Neurosci. Res. 1995, 41, 828.
12. Kozikowski, A. P.; Xia, Y. J. Am. Chem. Soc. 1989, 111, 4116.
13. For a related approach, see: Qian, L. G.; Ji, R. Y. Tetrahedron Lett 1989, 2089.
14. Yamada, F.; Kozikowski, A. P.; Reddy, E. R; Pang, Y.-P.; Miller, J. H.; McKinney, M. J. Am Chem. Soc. 1991, 113, 4695.
15. Kozikowski, A. P.; Tückmantel, W.; Saxena, A.; Doctor, B. P. Helv. Chim. Acta 1994, 77, 1256;
16. Kozikowski, A. P.; Campiani, G.; Tückmantel, W. Heterocycles 1994, 39, 101 and references therein.
17. Kozikowski, A. P.; Campiani, G.; Sun, L.-Q.; Aagaard, P.; McKinney, M. J. Org. Chem. 1993, 58, 7660.
18. Kozikowski, A. P.; Pang, Y.-P. J. Comp. Aided Molecular Design 1994, 8, 669.
19. Nelson, L. A. K.; Shaw, A. C.; Abrams, S. R. Tetrahedron 1991, 47, 3259.
20. 3) δ 12.97, 22.58, 24.58, 28.33, 42.32, 45.37, 49.91, 54.93, 112.64, 117.72, 120.23, 122.57, 134.46, 140.34, 141.40, 149.22, 164.14.
21. De La Hoz, D.; Doctor, B. P.; Ralston, J. S.; Rush, R S.; Wolfe, A. D. Life Sci. 1986, 39, 195.
22. Ellman, G. L.; Courtney, D.; Andres, V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 1, 88.