Relationships between the structure of 6-substituted 6,8-diazabicyclo[3.2.2]nonan-2-ones and their σ receptor affinity and cytotoxic activity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 4, 2009, Pages 1445-1455

  Holl, Ralph ^a   Schepmann, Dirk ^a   Bednarski, Patrick J ^b   Grünert, Renate ^b   Wünsch, Bernhard ^a  

^a INST OF REPRO MED OF THE UNIV   (Germany)

^b UNIVERSITY MEDICINE GREIFSWALD   (Germany)

Author keywords

Cytotoxicity; Diazabicyclo 3.2.2 nonanes; Sigma receptor ligands; Structure activity relationships

Indexed keywords

6,8 DIAZABICYCLO[3.2.2]NONANE DERIVATIVE; NONANE; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ACETALIZATION; ALKYLATION; ARTICLE; ARYLATION; CANCER INHIBITION; CYTOTOXICITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

ALKANES; ANIMALS; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; CELL GROWTH PROCESSES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; GUINEA PIGS; HUMANS; KETONES; PROTEIN BINDING; RATS; RECEPTORS, SIGMA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60049095946     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.012     Document Type: Article

References (18)

1. Walker J.M., Bowen W.D., Walker F.O., Matsumoto R.R., De Costa B., and Rice K.C. Pharmacol. Rev. 42 (1990) 355
2. Quirion R., Bowen W.D., Itzhak Y., Junien J.L., Musacchio J.M., Rothman R.B., Su T.P., Tam S.W., and Taylor D.P. Trends Pharmacol. Sci. 13 (1992) 85
3. Bowen W.D. Pharm. Acta Helv. 74 (2000) 211
4. Hanner M., Moebius F.F., Flandorfer A., Knaus H., Striessnig J., Kempner E., and Glossman H. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 8072
5. Aydar E., Palmer C.P., Klyachko V.A., and Jackson M.B. Neuron 34 (2002) 399
6. Aydar E., Palmer C.P., and Djamgoz M.B. Cancer Res. 64 (2004) 5029
7. Glennon R.A., Ablordeppey S.Y., Ismaiel A.M., El-Ashmawy M.B., Fischer J.B., and Howie K.B. J. Med. Chem. 37 (1994) 1214
8. Holl, R.; Schepmann, D.; Grünert, R.; Bednarski, P. J.; Wünsch, B. Bioorg. Med. Chem. 2009, 17, 777.
9. Jung B., Englberger W., and Wünsch B. Arch. Pharm. Pharm. Med. Chem. 338 (2005) 281
10. Renaud J., Bischoff S.F., Buhl T., Floersheim P., Fournier B., Geiser M., Halleux C., Kallen J., Keller H., and Ramage P. J. Med. Chem. 48 (2005) 364
11. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 438
12. Wirt U., Schepmann D., and Wünsch B. Eur. J. Org. Chem. (2007) 462
13. Colabufo N.A., Berardi F., Contino M., Niso M., Abate C., Perrone R., and Tortorella V. Naunyn Schmiedebergs Arch. Pharmacol. 370 (2004) 106
14. Bracht K., Boubakari, Grunert R., and Bednarski P.J. Anticancer Drugs 17 (2006) 41
15. Bradford M.M. Anal. Biochem. 72 (1976) 248
16. DeHaven-Hudkins D.L., Fleissner L.C., and Ford-Rice F.Y. Eur. J. Pharmacol. Mol. Pharmacol. Sect. 227 (1992) 371
17. Mach R.H., Smith C.R., and Childers S.R. Life Sci. 57 (1995) PL57
18. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099