4-((2-halogeno-5-pyridyl)dimethylsilyl)phenylboronic acids: New potential building blocks for the synthesis of silicon-containing drugs

Organometallics

Volumn 28, Issue 11, 2009, Pages 3218-3224

  Troegel, Dennis ^a   Möller, Frank ^a   Burschka, Christian ^a   Tacke, Reinhold ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOPHENOL; DIMETHYLSILANE; ELEMENTAL ANALYSIS; MULTINUCLEAR NMR; PHENYLBORONIC ACIDS; POTENTIAL BUILDING BLOCKS; PYRIDYL; SINGLE CRYSTAL X-RAY DIFFRACTION; SUZUKI-MIYAURA COUPLING REACTION;

CHEMICAL SENSORS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION ANALYSIS;

ORGANIC ACIDS;

EID: 66349112847     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900175m     Document Type: Article

References (47)

1. Hall, D. G. In Boronic Acids-Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 1-99, and references therein.
2. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
3. Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97.
4. Suzuki, A. J. Organomet. Chem. 2002, 653, 83-90.
5. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
6. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133-173.
7. Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527-538.
8. Dahlhoff, W. V.; Köster, R. Synthesis 1980, 936-937.
9. Evans, D. A.; Polniaszek, R. P. Tetrahedron Lett. 1986, 27, 5683-5686.
10. Gypser, A.; Michel, D.; Nirschl, D. S.; Sharpless, K. B. J. Org. Chem. 1998, 63, 7322-7327.
11. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem. 1996, 108, 2038-2050; Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922.
12. Gray, C. W., Jr.; Houston, T. A. J. Org. Chem. 2002, 67, 5426-5428.
13. Yang, W.; Gao, X.; Wang, B. Med. Res. Rev. 2003, 23, 346-368.
14. Paramore, A.; Frantz, S. Nature Rev. Drug Discovery 2003, 2, 611-612.
15. Ahmed, V.; Liu, Y.; Silvestro, C.; Taylor, S. D. Bioorg. Med. Chem. 2006, 14, 8564-8573.
16. Deng, X.; Mayeux, A.; Cai, C. J. Org. Chem. 2002, 67, 5279-5283.
17. Fournier, J.-H.; Maris, T.; Wuest, J. D.; Guo, W.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002-1006.
18. Deng, X.; Cai, C. Tetrahedron Lett. 2003, 44, 815-817.
19. Kim, J.-U.; Lee, H.-B.; Shin, J.-S.; Kim, Y.-H.; Joe, Y.-K.; Oh, H.-Y.; Park, C.-G.; Kwon, S.-K. Synth. Met. 2005, 150, 27-32.
20. You, Y.; An, C.-G.; Lee, D.-S.; Kim, J.-J.; Park, S. J. J. Mater. Chem. 2006, 16, 4706-4713.
21. Recent reviews dealing with silicon-based drugs: (a) Bains, W.; Tacke, R. Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
22. Showell, G. A.; Mills, J. S. Drug Discovery Today 2003, 8, 551-556.
23. Mills, J. S.; Showell, G. A. Expert Opin. Investig. Drugs 2004, 13, 1149-1157.
24. Sieburth, S. McN.; Chen, C.-A. Eur. J. Org. Chem. 2006, 311-322.
25. Gately, R.; West, R. Drug Dev. Res. 2007, 68, 156-163.
26. Franz, A. K. Curr. Opin. Drug Discovery Dev. 2007, 10, 654-671.
27. Recent original publications dealing with sila-substituted drugs: (a) Showell, G. A.; Barnes, M. J.; Daiss, J. O.; Mills, J. S.; Montana, J. G.; Tacke, R.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2006, 16, 2555-2558.
28. Ilg, R.; Burschka, C.; Schepmann, D.; Wünsch, B.; Tacke, R. Organometallics 2006, 25, 5396-5408.
29. Büttner, M. W.; Burschka, C.; Daiss, J. O.; Ivanova, D.; Rochel, N.; Kammerer, S.; Peluso-Iltis, C.; Bindler, A.; Gaudon, C.; Germain, P.; Moras, D.; Gronemeyer, H.; Tacke, R. ChemBioChem 2007, 8, 1688-1699.
30. Tacke, R.; Popp, F.; Müller, B.; Theis, B.; Burschka, C.; Hamacher, A.; Kassack, M. U.; Schepmann, D.; Wünsch, B.; Jurva, U.; Wellner, E. ChemMedChem 2008, 3, 152-164.
31. Warneck, J. B.; Cheng, F. H. M.; Barnes, M. J.; Mills, J. S.; Montana, J. G.; Naylor, R. J.; Ngan, M.-P.; Wai, M.-K.; Daiss, J. O.; Tacke, R.; Rudd, J. A. Toxicol. Appl. Pharmacol. 2008, 232, 369-375.
32. Denton, T. T.; Zhang, X.; Cashman, J. R. J. Med. Chem. 2005, 48, 224-239.
33. Hocke, C.; Prante, O.; Löber, S.; Hübner, H.; Gmeiner, P.; Kuwert, T. Bioorg. Med. Chem. Lett. 2005, 15, 4819-4823.
34. Wiles, J. A.; Song, Y.; Wang, Q.; Lucien, E.; Hashimoto, A.; Cheng, J.; Marlor, C. W.; Ou, Y.; Podos, S. D.; Thanassi, J. A.; Thoma, C. L.; Deshpande, M.; Pucci, M. J.; Bradbury, B. J. Bioorg. Med. Chem. Lett. 2006, 16, 1277-1281.
35. Kahn, M. G. C.; Konde, E.; Dossou, F.; Labaree, D. C.; Hochberg, R. B.; Hoyte, R. M. Bioorg. Med. Chem. Lett. 2006, 16, 3454-3458.
36. Johns, B. A.; Gudmundsson, K. S.; Allen, S. H. Bioorg. Med. Chem. Lett. 2007, 17, 2858-2862.
37. Gao, Y.; Horti, A. G.; Kuwabara, H.; Ravert, H. T.; Hilton, J.; Holt, D. P.; Kumar, A.; Alexander, M.; Endres, C. J.; Wong, D. F.; Dannals, R. F. J. Med. Chem. 2007, 50, 3814-3824.
38. Andersen, M. W.; Hildebrandt, B.; Köster, G.; Hoffmann, R. W. Chem. Ber. 1989, 122, 1777-1782.
39. Coutts, S. J.; Adams, J.; Krolikowski, D.; Snow, R. J. Tetrahedron Lett. 1994, 35, 5109-5112.
40. Falck, J. R.; Bondlela, M.; Venkataraman, S. K.; Srinivas, D. J. Org. Chem. 2001, 66, 7148-7150.
41. Edsall, R. J.; Harris, H. A.; Manas, E. S.; Mewshaw, R. E. Bioorg. Med. Chem. 2003, 11, 3457-3474.
42. Mewshaw, R. E.; Edsall, R. J., Jr.; Yang, C.; Manas, E. S.; Xu, Z. B.; Henderson, R. A.; Keith, J. C., Jr.; Harris, H. A. J. Med. Chem. 2005, 48, 3953-3979.
43. The hydrogen-bonding systems were analyzed by using the program system PLATON: (a) Spek, A. L., PLATON; University of Utrecht, Utrecht, The Netherlands, 1998.
44. Spek, A. L. Acta Crystallogr., Sect. A 1990, 46 (Supplement), C34.
45. Sheldrick, G. M. SHELXS-97; University of Göttingen, Göttingen, Germany, 1997.
46. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473.
47. Sheldrick, G. M. SHELXL-97; University of Göttingen, Göttingen, Germany, 1997.