Silanediol protease inhibitors: From conception to validation

European Journal of Organic Chemistry

Volumn , Issue 2, 2006, Pages 311-322

  Sieburth, Scott McN ^a   Chen, Chien An ^b  

^a Temple University   (United States)

^b LUNDBECK RESEARCH USA   (United States)

Author keywords

Drug design; Hydrolases; Inhibitors; Peptidomimetics; Proteases; Silanes; Silicon

Indexed keywords

EID: 31144452136     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500508     Document Type: Short Survey

References (95)

1. W. Bains, Astrobiology 2004, 4, 137-167.
2. R. J. Fessenden, J. S. Fessenden, Adv. Drug Res. 1967, 4, 95-132.
3. M. Zbik, M. Jasieniak, R. S. C. Smart, Meteorit. Planet. Sci. 2000, 35, 943-947.
4. S. Barcza, in: Silicon Chemistry (Eds.: E. R. Corey, J. Y. Corey, P. P. Gaspar), Wiley, New York, 1988, p. 135-144.
5. R. Tacke, H. Linoh, in: The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), John Wiley & Sons, New York, 1989, p. 1143-1206.
6. R. Tacke, S. A. Wagner, in: The Chemistry of Organic Silicon Compounds (Eds.: Z. Rappoport, Y. Apeloig), John Wiley & Sons, New York, 1998, p. 2363-2400.
7. G. A. Showell, J. S. Mills, Drug Discov. Today 2003, 8, 551-556.
8. W. Bains, R. Tacke, Curr. Opin. Drug Discovery Dev. 2003, 6, 526-543.
9. L. Collste, T. Berlin, B. von Garrelts, I. Granberg, R. Lewander, Euro. Urol. 1981, 7, 85-88.
10. K. Azizuddin, K. Kalka, S.-M. Chiu, N. Ahmad, H. Mukhtar, D. Separovic, Int. J. Oncol. 2001, 18, 411-415.
11. P. A. Thompson, S. L. Berg, A. Aleksic, J. Z. Kerr, L. McGuffey, R. Dauser, J. G. Nüchtern, F. Hausheer, S. M. Blaney, Cancer Chemother. Pharmacol. 2004, 55, 527-532.
12. E. Boven, A. H. Van Hattum, I. Hoogsteen, H. M. M. Schluper, H. M. Pinedo, Ann. N. Y. Acad. Sci. 2000, 922, 175-177.
13. A. Daud, N. Valkov, B. Centeno, J. Derderian, P. Sullivan, P. Munster, P. Urbas, R. C. DeConti, E. Berghorn, Z. Liu, F. Hausheer, D. Sullivan, Clin. Canc. Res. 2005, 11, 3009-3016.
14. R. Tacke, T. Schmid, M. Penka, C. Burschka, W. Bains, J. Warneck, Organometallics 2004, 23, 4915-4923.
15. R. Tacke, H. Linoh, L. Ernst, U. Moser, E. Mutschier, S. Sarge, H. K. Cammenga, G. Lambrecht, Chem. Ber. 1987, 120, 1229-1237.
16. W. K. Moberg, G. S. Basarab, J. Cuomo, P. H. Liang, in: Pesticide Science and Biotechnology (Eds.: R. Greenhalgh, T. R. Roberts), Blackwell Scientific, Boston, 1986, p. 57-60.
17. S. McN. Sieburth, C. J. Manly, D.W. Gammon, Pestic. Sci. 1990, 28, 289-307.
18. G. Raabe, J. Michl, in: The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), John Wiley & Sons, New York, 1989, p. 1015-1142.
19. W. J. Leigh, R. Boukherroub, C. Kerst, J. Am. Chem. Soc. 1998, 120, 9504-9512.
20. R. N. Meals, F. M. Lewis, Silicones, Reinhold, New York, 1959.
21. Handbook of Proteolytic Enzymes (Eds.: A. J. Barrett, N. D. Rawlings, J. F. Woessner, Jr.), Bath Press, Bath, England, 1998.
22. A. S. Ripka, D. H. Rich, Curr. Opin. Chem. Biol. 1998, 2, 441-452.
23. R. E. Babine, S. L. Bender, Chem. Rev. 1997, 97, 1359-1472.
24. D. Leung, G. Abbenante, D. P. Fairlie, J. Med. Chem. 2000, 43, 305-341.
25. W. Dilthey, F. Eduardoff, Ber. Dtsch. Chem. Ges. 1904, 37, 1139-1142.
26. G. Martin, F. S. Kipping, J. Chem. Soc. 1909, 95, 302-314.
27. A search of the Beilstein CrossFire database finds 147 structures.
28. E. G. Rochow, Silicon and Silicones, Springer-Verlag, New York, 1987.
29. R. Tacke, T. Schmid, M. Merget, Organometallics 2005, 24, 1780-1783.
30. S. Cassidy, Manufacturing Chemist 1989, December issue, p. 51.
31. M. Cypryk, S. Rubinsztajn, H. Chojnowski, J. Organomet. Chem. 1993, 446, 91-97.
32. J. C. Carpenter, J. A. Cella, S. B. Dorn, Environ. Sci. Technol. 1995, 29, 864-868.
33. R. G. Lehmann, S. Varaprath, C. L. Frye, Environ. Toxicol. Chem. 1994, 13, 1061-1064.
34. I. Temmerman, P. Sandra, M. Verzele, J. High Resolut. Chromatogr. 1985, 8, 513-515.
35. J. K. Haken, N. Harahap, R. P. Burford, J. Coatings Techn. 1987, 59, 73-78.
36. B. Dejak, Z. Lasocki, W. Mogilnicki, Bull. Acad. Polon. Sci. Sér. Sci. Chim. 1969, 17, 571-574.
37. C. Eaborn, N. H. Hartshorne, J. Chem. Soc. 1955, 549-555.
38. P. D. Lickiss, Adv. Inorg. Chem. 1995, 42, 147-262.
39. B. M. Trost, C. G. Caldwell, E. Murayama, D. Heissler, J. Org. Chem. 1983, 48, 3252-3265.
40. M. Bodanszky, Peptide Chemistry: A Practical Textbook, Springer-Verlag, New York, 1988.
41. I. Fleming, J. Dunoguès, R. Smithers, Org. React. (NY) 1989, 37, 57-575.
42. W. Uhlig, Chem. Ber. 1996, 129, 733-739.
43. C. Eaborn, J. Chem. Soc. 1956, 4858-4864.
44. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis 3rd ed., John Wiley & Sons, New York, 1999.
45. D. W. Cushman, H. S. Cheung, E. F. Sabo, M. A. Ondetti, Biochemistry 1977, 16, 5484-5491.
46. S. A. DePriest, D. Mayer, C. B. Naylor, G. R. Marshall, J. Am. Chem. Soc. 1993, 115, 5372-5384.
47. R. G. Almquist, W.-R. Chao, M. E. Ellis, H. L. Johnson, J. Med. Chem. 1980, 23, 1392-1398.
48. R. F. Meyer, E. D. Nicolaides, F. J. Tinney, E. A. Lunney, A. Holmes, M. L. Hoefle, R. D. Smith, A. D. Essenburg, H. R. Kaplan, R. G. Almquist, J. Med. Chem. 1981, 24, 964-969.
49. R. G. Almquist, J. Crase, C. Jennings-White, R. F. Meyer, M. L. Hoefle, R. D. Smith, A. D. Essenburg, H. R. Kaplan, J. Med. Chem. 1982, 25, 1292-1299.
50. A. M. Mutahi, Ph. D. Thesis, SUNY Stony Brook, 1996.
51. A. Wlodawer, J. Vondrasek, Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 249-284.
52. J. W. Erickson, M. A. Eissenstat, in: Proteases of Infectious Agents (Ed.: B. M. Dunn), Academic, New York, 1999, p. 1-60.
53. D. J. Kempf, Methods Enzymol. 1994, 241, 334-354.
54. D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739.
55. S. McN. Sieburth, C.-A. Chen, Synlett 1995, 928-930.
56. J. Chojnowski, in: Siloxane Polymers (Ed.: S. J. Clarson, J. A. Semlyen), Prentice Hall, Englewood Cliffs, NJ, 1993, p. 1-71.
57. R. J. Field, E. W. Olson, J. Non-Cryst. Solids 2001, 285, 194-201.
58. C.-A. Chen, S. McN. Sieburth, A. Glekas, G. W. Hewitt, G. L. Trainor, S. Erickson-Viitanen, S. S. Garber, B. Cordova, S. Jeffrey, R. M. Klabe, Chem. Biol. 2001, 8, 1161-1166.
59. R. Bone, J. P. Vacca, P. S. Anderson, M. K. Holloway, J. Am. Chem. Soc. 1991, 113, 9382-9384.
60. S. McN. Sieburth, T. Nittoli, A. M. Mutahi, L. Guo, Angew. Chem. Int. Ed. Engl. 1998, 37, 812-814.
61. M. wa Mutahi, T. Nittoli, L. Guo, S. McN. Sieburth, J. Am. Chem. Soc. 2002, 124, 7363-7375.
62. J. Kim, G. Hewitt, P. Carroll, S. McN. Sieburth, J. Org. Chem. 2005, 70, 5781-5789.
63. J. Kim, S. McN. Sieburth, Bioorganic Med. Chem. Lett. 2004, 14, 2853-2856.
64. B. W. Matthews, Acc. Chem. Res. 1988, 21, 333-340.
65. C. Eaborn, J. Chem. Soc. 1952, 2846-2849.
66. I. Fleming, in: Comprehensive Organic Chemistry (Eds.: D. Barton, W. D. Ollis), Pergamon, New York, 1979, p. 541-686.
67. Y.-R. Luo, Handbook of Bond Dissociation Energies, in: Organic Compounds, CRC, New York, 2003.
68. D, H. Juers, J. Kim, B. W. Matthews, S. McN. Sieburth, manuscript submitted.
69. H. M. Holden, D. E. Tronrud, A. F. Monzingo, L. H. Weaver, B. W. Matthews, Biochemistry 1987, 26, 8542-8553.
70. J. Kim, S. McN. Sieburth, J. Org. Chem. 2004, 69, 3008-3014.
71. B. Marciniec, Comprehensive Handbook on Hydrosilylation, Pergamon, New York, 1992.
72. I. Ojima, in: The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1989, p. 1479-1525.
73. I. Ojima, Z. Li, J. Zhu, in: The Chemistry of Organic Silicon Compounds (Eds.: Z. Rappoport, Y. Apeloig), Wiley, New York, 1998, p. 1687-1792.
74. T. Murai, T. Oda, F. Kimura, H. Onishi, T. Kanda, S. Kato, J. Chem. Soc: Chem. Commun. 1994, 2143-2144.
75. T. Murai, F. Kimura, K. Tsutsui, K. Hasegawa, S. Kato, Organometallics 1998, 17, 926-932.
76. D. Wang, T. H. Chan, Science of Synthesis 2002, 4, 481-498.
77. P. Beak, W. J. Zajdel, D. B. Reitz, Chem. Rev. 1984, 84, 471-523.
78. P. J. Jessup, C. B. Petty, J. Roos, L. E. Overman, Org. Svnth. Coll. Vol. 1988, 6, 95-101.
79. G. W. Hewitt, J. J. Somers, S. McN. Sieburth, Tetrahedron Lett. 2000, 41, 10175-10179.
80. S. McN. Sieburth, J. J. Somers, H. K. O'Hare, Tetrahedron 1996, 52, 5669-5682.
81. S. McN. Sieburth, J. J. Somers, Tetrahedron 1996, 52, 5683-5690.
82. A. G. Brook, J. M. Duff, J. Am. Chem. Soc. 1974, 96, 4692-4693.
83. J. M. Duff, A. G. Brook, Can. J. Chem. 1977, 55, 2589-2600.
84. A. G. Brook, Acc. Chem. Res. 1974, 7, 77-84.
85. Guodong Liu, research notes, Temple University.
86. S. McN. Sieburth, H. K. O'Hare, J. Xu, Y. Chen, G. Liu, Org. Lett. 2003, 5, 1859-1861.
87. S. Wu, S. Lee, P. Beak, J. Am. Chem. Soc. 1996, 118, 715-721.
88. M. J. Dearden, C. R. Firkin, J.-P. R. Hermet, P. O'Brien, J. Am. Chem. Soc. 2002, 124, 11870-11871.
89. G. Liu, S. McN. Sieburth, Org. Lett. 2003, 5, 4677-4679.
90. S. Mignani, D. Damour, J.-P. Bastart, G. Manuel, Synth. Commun. 1995, 25, 3855-3861.
91. H. C. Brown, P. K. Jadhav, A. K. Mandal, J. Org. Chem. 1982, 47, 5047-5083.
92. N. S. Duesbery, C. P. Webb, S. H. Leppla, V. M. Gordon, K. R. Kumpel, T. D. Copeland, N. G. Ahn, M. K. Oskarsson, K. Fukasawa, K. D. Paull, G. F. V. Woude, Science 1998, 280, 734-737.
93. P. A. Wender, S. T. Handy, D. L. Wright, Chem. Indust. 1997, 765-769.
94. J. C. Powers, J. L. Asgian, O. D. Ekici, K. E. James, Chem. Rev. 2002, 102, 4639-4750.
95. H. Nishiyama, K. Itoh, in: Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 111-143.