Synthesis and structure-affinity relationships of 1,3,5-alkylsubstituted cyclohexylamines binding at NMDA receptor PCP site

European Journal of Medicinal Chemistry

Volumn 35, Issue 6, 2000, Pages 555-565

  Jirgensons, Aigars ^a   Kauss, Valerjans ^a   Kalvinsh, Ivars ^a   Gold, Markus R ^b   Danysz, Wojciech ^b   Parsons, Chris G ^b   Quack, Gunter ^b  

^a LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

^b MERZ PHARMACEUTICALS GMBH   (Germany)

Author keywords

Cyclohexylamines; Hansch analysis; NMDA receptor; PCP

Indexed keywords

CYCLOHEXYLAMINE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PHENCYCLIDINE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL STRUCTURE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0033918045     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(00)00153-7     Document Type: Article

References (30)

1. Danysz W., Parsons C.G., Bresink I., Quack G. Drug News Perspect. 8:1995;261-277.
2. Kemp J.A., Foster A.C., Wong E.H.F. Trends Neurosci. 10:1987;294-298.
3. Kroemer R.T., Koutsilieri E., Hecht P., Liedl K.R., Riederer P., Kornhuber J. J. Med. Chem. 41:1998;393-400.
4. Kornhuber J., Bormann J., Hubers M., Rusche K., Riederer P. Eur. J. Pharmacol. Mol. Pharmacol. 206:1991;297-300.
5. Firrell N.F., Hickmott P.W. J. Chem. Soc. C. 1970;716-719.
6. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis, 1st ed. 1992;Pergamon Press, NY.
7. Helmchen G., Hoffman R.W., Hulzez J., Schaumann E. (Eds.), Methods of Organic Chemistry Vol. 2 (Houben-Weyl), Stereoselective synthesis, Georg Thieme Verlag, Stuttgart, 1996, D.1.3.1.
8. Hassner A., Fibiger R., Andisik D. J. Org. Chem. 49:1984;4237-4244.
9. Rickborn B., Wuesthoff M.T. J. Am. Chem. Soc. 92:1970;6894-6904.
10. Koziara A., Zwierzak A. Tetrahedron Lett. 28:1987;6513-6516.
11. Corey E.J., Feiner N.F. J. Org. Chem. 45:1980;765-780.
12. Senda Y., Ishiyama J., Imaizumi S. Tetrahedron. 31:1975;1601-1605.
13. Eliel E.L., Wilen S.H., Mander L.N. (Eds.), Stereochemistry of Organic Componds, John Wiley & Sons, Inc., NY, 1994, p. 710.
14. Tavernier D., Anteunis J.O. Org. Magn. Res. 11:1978;628-631.
15. Zschuke A., Borsdorf R., Remane H., Werner H. Z. Chem. 12:1972;231-232.
16. Parsons C.G., Danysz W., Bartmann A., Spielmans P., Frankiewicz T., Hesselink M., Eilbacher B., Quack G. Neuropharmacology. 38:1999;85-108.
17. Leeson P.D., Carling R.W., James K., Smith J.D., Moore K.W., Wong E.H.F., Baker R. J. Med. Chem. 33:1990;1296-1305.
18. Monn J.A., Thurkauf A., Matson M.V., Jacobson A.E., Rice K.C. J. Med. Chem. 33:1990;1069-1076.
19. Hogberg T., Norinder U., in: Krogsgaard-Larsen P., Liljefors T., Madsen U. (Eds.), A Textbook of Drug Design and Development, 2nd ed., Harwood Academic Publishers GmbH, The Netherlands, 1996, pp. 94-130.
20. Leo A., Jow P.Y.C., Silipo C., Hansch C. J. Med. Chem. 18:1975;865-868.
21. Frank R.L., Hall H.K. J. Am. Chem. Soc. 72:1950;1645-1648.
22. Hiegel G.A., Burk P. J. Org. Chem. 38:1973;3637-3639.
23. Posner G.H., Frye L.L. Isr. J. Chem. 24:1984;88-92.
24. Lemiere G.L., van Osselaer T.A., Anderweireldt F.C. Bull. Soc. Chim. Belg. 87:1978;771-782.
25. House O.H., Wilkins J.M. J. Org. Chem. 41:1976;4031-4033.
26. House O.H., Fischer W.F. J. Org. Chem. 33:1968;949-954.
27. Chiurdoglu G., Maquestiau A. Bull. Soc. Chim. Belg. 63:1954;357-378.
28. Zaidlewicz M., Uzarewicz A. Roczniki Chem. 45:1971;1187-1194.
29. Miyajima S., Simamura O. Bull. Chem. Soc. Japan. 48:1975;526-530.
30. Hamlin K.E., Freifelder M. J. Am. Chem. Soc. 75:1953;369-373.