Syntheses and pharmacological characterization of achiral and chiral enantiopure C/Si/Ge-analogous derivatives of the muscarinic antagonist cycrimine: A study on C/Si/Ge bioisosterism

Journal of Organometallic Chemistry

Volumn 640, Issue 1-2, 2001, Pages 140-165

  Tacke, Reinhold ^a   Kornek, Thomas ^a   Heinrich, Tilman ^a   Burschka, Christian ^a   Penka, Martin ^a   Pülm, Melanie ^a   Keim, Christine ^b   Mutschler, Ernst ^b   Lambrecht, Günter ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY HOSPITAL FRANKFURT   (Germany)

Author keywords

C Si Ge bioisosterism; Chirality; Germanium; Muscarinic antagonists; ORD; Silicon

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0000375497     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)01179-2     Document Type: Article

References (23)

1. Tacke R., Reichel D., Kropfgans M., Jones P.G., Mutschler E., Gross J., Hou X., Waelbroeck M., Lambrecht G. Organometallics. 14:1995;251.
2. Tacke R., Reichel D., Günther K., Merget S. Z. Naturforsch. 50b:1995;568.
3. Tacke R., Reichel D., Jones P.G., Hou X., Waelbroeck M., Gross J., Mutschler E., Lambrecht G. J. Organomet. Chem. 521:1996;305.
4. Mutschler E., Ensinger H.A., Gross J., Leis A., Mendla K., Moser U., Pfaff O., Reichel D., Rühlmann K., Tacke R., Waelbroeck M., Wehrle J., Lambrecht G. Giardinà D., Piergentili A., Pigini M. Perspectives in Receptor Research. 1996;51-65 Elsevier, Amsterdam.
5. Caulfield M.P., Birdsall N.J.M. Pharmacol. Rev. 50:1998;279.
6. A. Leis, PhD Thesis, Technische Universität Dresden, 1994.
7. Tacke R., Kropfgans M., Tafel A., Wiesenberger F., Sheldrick W.S., Mutschler E., Egerer H., Rettenmayr N., Gross J., Waelbroeck M., Lambrecht G. Z. Naturforsch. 49b:1994;898.
8. Recent short review: Tacke R., Heinrich T., Kornek T., Merget M., Wagner S.A., Gross J., Keim C., Lambrecht G., Mutschler E., Beckers T., Bernd M., Reissmann T. Phosphorus, Sulfur Silicon. 150-151:1999;69.
9. Recent original papers: (a) R. Tacke, M. Merget, R. Bertermann, M. Bernd, T. Beckers, T. Reissmann, Organometallics 19 (2000) 3486;
10. (b) M. Merget, K. Günther, M. Bernd, E. Günther, R. Tacke, J. Organomet. Chem. 628 (2001) 183.
11. 2 and subsequent alkylation with cyclopentyl bromide) failed.
12. 2-N torsion angles: 2(S)-3a·(R,R)-HOOC-CHR-CHR-COOH (R=O-CO-Ph), -154.2(2)° (cation 1) and -174.4(2)° (cation 2); (R)-4b, -165.2(3)° (cation 1) and -166.9(3)° (cation 2); (R)-4c, -166.7(3)° (cation 1) and -166.5(3)° (cation 2).
13. All experiments described in Section 2.4 have been repeated leading to reproducible results. Thus, an exchange of the samples can be definitely excluded.
14. Waelbroeck M., Camus J., Tastenoy M., Lambrecht G., Mutschler E., Tacke R., Christophe J. Eur. J. Pharmacol. Mol. Pharm. Sect. 189:1990;135.
15. Waelbroeck M., Camus J., Tastenoy M., Mutschler E., Strohmann C., Tacke R., Lambrecht G., Christophe J. Chirality. 3:1991;118.
16. Tacke R., Pikies J., Linoh H., Rohr-Aehle R., Gönne S. Liebigs Ann. Chem. 1987;51.
17. Tacke R., Becker B. J. Organomet. Chem. 354:1988;147.
18. G.M. Sheldrick, SHELXS-97, University of Göttingen, Göttingen, Germany, 1997.
19. Sheldrick G.M. Acta Crystallogr. A. 46:1990;467.
20. G.M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen, Germany, 1997.
21. Dörje F., Wess J., Lambrecht G., Tacke R., Mutschler E., Brann M.R. J. Pharmacol. Exp. Ther. 256:1991;727.
22. Waelbroeck M., Lazareno S., Pfaff O., Friebe T., Tastenoy M., Mutschler E., Lambrecht G. Br. J. Pharmacol. 119:1996;1319.
23. Cheng Y., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099.