Evaluation of short-tether bis-THA AChE inhibitors. A further test of the dual binding site hypothesis

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 2, 1999, Pages 351-357

  Carlier, Paul R ^a   Han, Yi Fan ^a   Chow, Ella S H ^a   Li, Crystal P L ^a   Wang, Hong ^a   Xuan Lieu, Thuy ^a   Sum Wong, Hau ^a   Pang, Yuan Ping ^b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b MAYO CLINIC CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BIS(4 ALLYLDIMETHYLAMMONIUMPHENYL)PENTAN 3 ONE DIBROMIDE; ACETYLCHOLINESTERASE; CHOLINESTERASE; TACRINE DERIVATIVE;

ALKYLATION; ANIMAL TISSUE; BINDING SITE; DRUG BINDING; DRUG POTENCY; DRUG SYNTHESIS; ENZYME BINDING; FRONTAL CORTEX; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; SHORT SURVEY; STRUCTURE ACTIVITY RELATION;

EID: 0033044911     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00213-2     Document Type: Article

References (15)

1. Pang, Y.-P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. J. Biol. Chem. 1996, 271, 23646.
2. Pang, Y.-P.; Kozikowski, A. P. J. Comput.-Aided Mol. Design 1994, 8, 669.
3. Pang, Y.-P.; Hong, F.; Quiram, P.; Jelacic, T.; Brimijoin, S. J. Chem. Soc. Perkin Trans. I 1997, 171.
4. Galanakis, D.; Davis, C. A.; Herrero, B. D. R.; Ganellin, C. R.; Dunn, P. M.; Jenkinson, D. H. J. Med. Chem. 1995, 38, 595.
5. Galanakis, D.; Davis, C. A.; Ganellin, C. R.; Dunn, P. M. J. Med. Chem. 1996, 39, 359.
6. Ganellin previously reported the efficacy of refluxing 1-pentanol solvent for the amination of 4-chloroquinoline by 1,n-diamines (ref. 5). Use of 1-butanol in amination reactions of 1 resulted in significantly longer reaction times.
7. 2 (optimized eluent).
8. Finlander, P.; Fischer, H. P.; Pedersen, E. B. Heterocycles 1985, 23, 1437.
9. Other higher yielding syntheses have been reported, but depend on commercially unavailable starting materials: a) Chong, R. J.; Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1986, 27, p. 5323 (70% yield). b) Reference 11 (55% yield).
10. Badger, G. M.; Hinde, R. W.; Matthews, W. E.; Spotswood, T. M. Australian J. Chem. 1963, 16, 732.
11. Cheng, X.-M.; Lee, C.; Klutchko, S.; Winters, T.; Reynolds, E. E.; Welch, K. M.; Flynn, M. A.; Dougherty, A. M. Bioorg. Med. Chem. Lett. 1996, 6, 2999.
12. Papadopoulou, M. V.; Rosenzweig, H. S.; Doddi, M.; Bloomer, W. D. Oncol. Res. 1994, 6, 439.
13. Ellman, G. L.; Courtney, K. D.; Andres, V. J.; Featherstone, R. M. Biochem. Pharm. 1961, 7, 88.
14. Harel, M.; Sussman, J. L.; Krejci, E.; Bon, S.; Chanal, P.; Massoulie, J.; Silman, I. Proc. Natl. Acad. Sci. USA 1992, 89, 10827.
15. Michalson, E. T.; D'Andrea, S.; Freeman, J. P.; Szmuszkovicz, J. Heterocycles 1990, 30, 415.