Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3220-3229

  Sim, Mui Mui ^a   Ganesan, Arasu ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542734984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Presented in part at the 2nd Australian Peptide Conference, Fraser Island, Australia, October 6-11, 1996, and the 4th Exploiting Molecular Diversity: Small Molecule Libraries for Drug Discovery, Coronado, CA, February 3-5, 1997.
2. Presented in part at the 2nd Australian Peptide Conference, Fraser Island, Australia, October 6-11, 1996, and the 4th Exploiting Molecular Diversity: Small Molecule Libraries for Drug Discovery, Coronado, CA, February 3-5, 1997.
3. Many excellent reviews of this area have appeared recently, for example: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
4. Many excellent reviews of this area have appeared recently, for example: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
5. (c) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
6. For reviews, see: (a) López, C. A.; Trigo, G. G. Adv. Heterocycl. Chem. 1985, 38, 177. (b) Edward, J. T. Chem. Org. Sulfur Comp. 1966, 2, 287. Ware, E. Chem. Rev. 1950, 46, 403.
7. For reviews, see: (a) López, C. A.; Trigo, G. G. Adv. Heterocycl. Chem. 1985, 38, 177. (b) Edward, J. T. Chem. Org. Sulfur Comp. 1966, 2, 287. Ware, E. Chem. Rev. 1950, 46, 403.
8. For reviews, see: (a) López, C. A.; Trigo, G. G. Adv. Heterocycl. Chem. 1985, 38, 177. (b) Edward, J. T. Chem. Org. Sulfur Comp. 1966, 2, 287. Ware, E. Chem. Rev. 1950, 46, 403.
9. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
10. Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937.
11. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835.
12. With an amide, the cyclization would be analogous to the well-known Edman degradation of peptides, which requires acid catalysis.
13. For representative examples, see: (a) Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821. (b) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. Biol. 1995, 2, 171. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240. Storer, R. Drug Discovery Today 1996, 1, 248.
14. For representative examples, see: (a) Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821. (b) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. Biol. 1995, 2, 171. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240. Storer, R. Drug Discovery Today 1996, 1, 248.
15. For representative examples, see: (a) Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821. (b) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. Biol. 1995, 2, 171. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240. Storer, R. Drug Discovery Today 1996, 1, 248.
16. For representative examples, see: (a) Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G.; Stylli, C. H.; Banks, M. N.; Tiller, P. R. Bioorg. Med. Chem. Lett. 1994, 4, 2821. (b) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chem. Biol. 1995, 2, 171. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240. Storer, R. Drug Discovery Today 1996, 1, 248.
17. For example, see: (a) Cheng, S.; Tarby, C. M.; Comer, D. D.; Williams, J. P.; Caporale, L. H.; Myers, P. L.; Boger, D. L. Bioorg. Med. Chem. 1996, 4, 727. (b) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193. (c) Studer, A.; Hadida, S.; Ferrito, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
18. For example, see: (a) Cheng, S.; Tarby, C. M.; Comer, D. D.; Williams, J. P.; Caporale, L. H.; Myers, P. L.; Boger, D. L. Bioorg. Med. Chem. 1996, 4, 727. (b) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193. (c) Studer, A.; Hadida, S.; Ferrito, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
19. For example, see: (a) Cheng, S.; Tarby, C. M.; Comer, D. D.; Williams, J. P.; Caporale, L. H.; Myers, P. L.; Boger, D. L. Bioorg. Med. Chem. 1996, 4, 727. (b) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193. (c) Studer, A.; Hadida, S.; Ferrito, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
20. (a) Abdel-Majid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595.
21. (b) Abdel-Majid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
22. (a) Ramanjulu, J. M.; Joullié, M. M. Synth. Commun. 1996, 26, 1379.
23. (b) Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. J. Org. Chem. 1996, 61, 6720.
24. A molar equivalent of triethylamine is added if the amine is in the form of an acid salt.
25. (a) Henichart, J. P.; Bernier, J. L. Synthesis 1980, 311.
26. (b) Jacobsen, N.; Toelberg, J. Synthesis 1986, 559.
27. (c) Stella, V.; Higuchi, T. J. Org. Chem. 1973, 38, 1527.
28. A similar conclusion was reached in the cyclization of peptide isocyanates and isothiocyanates: Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929. A valine derivative was partially cyclized at room temperature with triethylammonium hydrochloride: Nomoto, Y.; Takai, H.; Hirata, T.; Teranishi, M.; Ohno, T.; Kubo, K. Chem. Pharm. Bull. 1990, 38, 3014.
29. A similar conclusion was reached in the cyclization of peptide isocyanates and isothiocyanates: Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929. A valine derivative was partially cyclized at room temperature with triethylammonium hydrochloride: Nomoto, Y.; Takai, H.; Hirata, T.; Teranishi, M.; Ohno, T.; Kubo, K. Chem. Pharm. Bull. 1990, 38, 3014.
30. Solid-phase combinatorial approaches to dihydropyrimidine-2,4-diones and quinoxaline-2,4-diones have been reported: (a) Kolodziej, S. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277. (b) Buckman, B. O.; Mohan, R. Tetrahedron Lett. 1996, 37, 4439. (c) Smith, A. L.; Thomson, C. G.; Leeson, P. D. Bioorg. Med. Chem. Lett. 1996, 6, 1483.
31. Solid-phase combinatorial approaches to dihydropyrimidine-2,4-diones and quinoxaline-2,4-diones have been reported: (a) Kolodziej, S. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277. (b) Buckman, B. O.; Mohan, R. Tetrahedron Lett. 1996, 37, 4439. (c) Smith, A. L.; Thomson, C. G.; Leeson, P. D. Bioorg. Med. Chem. Lett. 1996, 6, 1483.
32. Solid-phase combinatorial approaches to dihydropyrimidine-2,4-diones and quinoxaline-2,4-diones have been reported: (a) Kolodziej, S. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277. (b) Buckman, B. O.; Mohan, R. Tetrahedron Lett. 1996, 37, 4439. (c) Smith, A. L.; Thomson, C. G.; Leeson, P. D. Bioorg. Med. Chem. Lett. 1996, 6, 1483.
33. These conditions were recently used in a similar cyclization: Hatam, M.; Köpper, S.; Martens, J. Heterocycles 1996, 43, 1653.
34. The same trend was observed in ref 15a.