1,4-Diazepanes derived from (S)-serine - Homopiperazines with improved σ1 (sigma) receptor affinity and selectivity

European Journal of Medicinal Chemistry

Volumn 44, Issue 2, 2009, Pages 519-525

  Bedürftig, Stephan ^a   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Receptor ligands; 1,4 Diazepanes; Homopiperazines

Indexed keywords

1,4 DIAZEPANE DERIVATIVE; 1,4 DIBENZYL DERIVATIVE; 5 (2,2 DIMETHOXYETHYL) 10 PHENYL 9 OXA 1,5 DIAZABICYCLO[5.3.0]DECANE 2,6 DIONE; 5 BENZYL 10 PHENYL 9 OXA 1,5 DIAZABICYCLO[5.3.0]DECANE 2,6 DIONE; [(1,4 DIBENZYL) 1,4 DIAZEPAN 2 YL]METHANOL; [1 BENZYL 4 (2,2 DIMETHOXYETHYL) 1,4 DIAZEPAN 2 YL]METHANOL; AMINE; CHLOROPROPIONAMIDE; HEXAHYDRO 1,4 DIAZEPINE DERIVATIVE; LEWIS ACID; METHYL 2 (3 CHLOROPROPANOYLAMINO) 3 HYDROXYPROPANOATE; PIPERAZINE DERIVATIVE; PROPIONAMIDE DERIVATIVE; SERINE; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SIGMA RECEPTOR LIGAND; UNCLASSIFIED DRUG;

AMINOLYSIS; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONFORMATIONAL TRANSITION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HOMOLOGATION; NONHUMAN; REACTION ANALYSIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

AZEPINES; PIPERAZINES; PROTEIN BINDING; RECEPTORS, SIGMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60349131311     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.03.033     Document Type: Article

References (21)

1. Hanner M., Moebius F.F., Flandorfer A., Knaus H.-G., Striessnig J., Kempner E., and Glossmann H. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 8072-8077
2. Kekuda R., Prasad P.D., Fei Y.-J., Leibach F.H., and Ganapathy V. Biochem. Biophys. Res. Commun. 229 (1996) 553-558
3. Seth P., Fei Y.-J., Li H.W., Huang W., Leibach F.H., and Ganapathy V. J. Neurochem 70 (1998) 922-931
4. Prasad P.D., Li H.W., Fei Y.-J., Ganapathy M.E., Fujita T., Plumley L.H., Yang-Feng T.L., Leibach F.H., and Ganapathy V. J. Neurochem. 70 (1998) 443-451
5. Brasili L. Pharm. Acta Helv. 74 (2000) 201-203
6. John C.S., Lim B.B., Vilner B.J., Geyer B.C., and Bowen W.D. J. Med. Chem. 41 (1998) 2445-2450
7. Abou-Gharbia M., Ablordeppey S.Y., and Glennon R. In: Bristol J.A. (Ed). Annual Reports in Medicinal Chemistry vol. 28 (1993), Academic, San Diego 1-10
8. Eiden F., and Lentzen H. Pharm. Unserer Zeit 25 (1996) 250-259
9. Monograph Igmesine Hydrochloride. Drugs Fut. 24 (1999) 133-140
10. Foster A., Wu H., Chen W., Williams W., Bowen W.D., Matsumoto R.R., and Coop A. Bioorg. Med. Chem. Lett. 13 (2003) 749-751
11. Matsumoto R.R., Liu Y., Lerner M., Howard E.W., and Bracket D.J. Eur. J. Pharmacol. 469 (2003) 1-12
12. Matsumoto R.R., McCracken K.A., Pouw B., Miller J., Bowen W.D., Williams W., and de Costa B.R. Eur. J. Pharmacol. 411 (2001) 261-273
13. Crawford K.W., and Bowen W.D. Cancer Res. 62 (2002) 313-322
14. Choi S.-R., Yang B., Plossl K., Chumpradit S., Wey S.P., Acton P.D., Wheeler K., Mach R.H., and Kung H.F. Nucl. Med. Biol. 28 (2001) 657-666
15. de Costa B.R., He X.-S., Linders J.T.M., Dominguez C., Gu Z.Q., Williams W., and Bowen W.D. J. Med. Chem. 36 (1993) 2311-2320
16. Bedürftig S., and Wünsch B. Bioorg. Med. Chem. 12 (2004) 3299-3311
17. Bieräugel H., Schoemaker H.E., Hiemstra H., and van Maarseveen J.H. Org. Biomol. Chem. 1 (2003) 1830-1832
18. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 438-448
19. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 4923-4930
20. Soukara S., Maier C., Predoiu U., Ehret A., Jackisch R., and Wünsch B. J. Med. Chem. 44 (2001) 2814-2826
21. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099-3108