Syntheses and pharmacological properties of the histaminic H1 antagonists sila-terfenadine-A, sila-terfenadine-B, disila-terfenadine, and sila-fexofenadine: A study on C/Si bioisosterism

Organometallics

Volumn 23, Issue 21, 2004, Pages 4915-4923

  Tacke, Reinhold ^a   Schmid, Thomas ^a   Penka, Martin ^a   Burschka, Christian ^a   Bains, William ^b   Warneck, Julie ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b Amedis Pharmaceuticals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CARBON; HYDROGEN; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CARBON ANALOGUES; CARBON ATOMS; CARDIOVASCULAR SIDE EFFECTS; PHARMACOLOGICAL PROPERTIES;

ORGANIC COMPOUNDS;

EID: 6344235650     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040084a     Document Type: Article

References (40)

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15. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
16. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
17. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
18. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
19. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
20. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
21. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
22. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
23. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
24. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
25. Recent publications dealing with C/Si bioisosterism: (a) Tacke, R.; Merget, M.; Bertermann, H.; Bernd, M.; Beckers, T.; Reissmann, T. Organometallics 2000, 19, 3486-3497. (b) Merget, M.; Günther, K.; Bernd, M.; Günther, E.; Tacke, R. J. Organomet. Chem. 2001, 628, 183-194. (c) Tacke, R.; Kornek, T.; Heinrich, T.; Burschka, C.; Penka, M.; Pülm, M.; Keim, C.; Mutschler, E.; Lambrecht, G. J. Organomet. Chem. 2001, 640, 140-165. (d) Tacke, R.; Schmid, T.; Burschka, C.; Penka, M.; Surburg, H. Organometallics 2002, 21, 113-120. (e) Tacke, R.; Handmann, V. I.; Kreutzmann, K.; Keim, C.; Mutschier, E.; Lambrecht, G. Organometallics 2002, 21, 3727-3732. (f) Tacke, R.; Handmann, V. I.; Bertermann, R.; Burschka, C.; Penka, M.; Seyfried, C. Organometallics 2003, 22, 916-924. (g) Tacke, R.; Schmid, T.; Hofmann, M.; Tolasch, T.; Francke, W. Organometallics 2003, 22, 870-372. (h) Schmid, T.; Daiss, J. O.; Ilg, R.; Surburg, H.; Tacke, R. Organometallics 2003, 22, 4343-4346. (i) Heinrich, T.; Burschka, C.; Warneck, J.; Tacke, R. Organometallics 2004, 23, 361-366. (j) Tacke, R.; Heinrich, T.; Bertermann, R.; Burschka, C.; Hamacher, A.; Kassack, M. U. Organometallics, in press. (k) Review: Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
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