Solid-phase synthesis of α-sulfonylamino amide derivatives based on Ugi-type condensation reaction using sulfonamides as amine input

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8467-8470

  Campian, Eugene ^a   Lou, Boliang ^a   Saneii, Hossain ^a  

^a Advanced SynTech   (United States)

Author keywords

Multi component condensation reaction; Solid phase synthesis; Sulfonamide

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; POLYMER; SULFONAMIDE;

ALKYLATION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; POLYMERIZATION; SOLID; SYNTHESIS;

EID: 0037131718     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02085-3     Document Type: Article

References (17)

1. Weber L. Drug Disc. Today. 7:2002;143-147.
2. For a recent review, see: Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210.
3. For representative examples, see: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175; (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583; © Park, S. J.; Keum, G.; Kang, S. Bang.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112; (d) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076; (e) Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969.
4. For representative examples, see: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175; (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583; © Park, S. J.; Keum, G.; Kang, S. Bang.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112; (d) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076; (e) Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969.
5. For representative examples, see: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175; (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583; © Park, S. J.; Keum, G.; Kang, S. Bang.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112; (d) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076; (e) Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969.
6. For representative examples, see: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175; (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583; © Park, S. J.; Keum, G.; Kang, S. Bang.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112; (d) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076; (e) Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969.
7. For representative examples, see: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175; (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583; © Park, S. J.; Keum, G.; Kang, S. Bang.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112; (d) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076; (e) Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969.
8. For representative examples, see: (a) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (b) Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573-6593; © Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712; (d) Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514.
9. For representative examples, see: (a) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (b) Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573-6593; © Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712; (d) Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514.
10. For representative examples, see: (a) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (b) Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573-6593; © Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712; (d) Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514.
11. For representative examples, see: (a) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754; (b) Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573-6593; © Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712; (d) Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509-1514.
12. For very recent examples of bioactive peptidomimetics containing α-sulfonylamino amide moieties, see: (a) Das, J. Kimball, S. D.; Reid, J. A.; Wang, T. C.; Lau, W. F. Roberts, D. G. M.; Seiler, S. M.; Schumacher, W. A.; Ogletree, M. L. Bioorg. Med. Chem. Lett. 2002, 12, 41-44; (b) Lin, L. S.; Kopka, I. E.; Mumford, R. A.; Magriotis, P. A.; Lanza, T., Jr.; Durette, P. L.; Kamenecka, T.; Young, D. N.; de Laszlo, S. E.; McCauley, E.; Van Riper, G.; Kidambi, U.; Egger, L. A.; Tong, X.; Lyons, K.; Vincent, S.; Stearns, R.; Colletti, A.; Teffera, Y.; Fenyk-Melody, J.; Schmidt, J. A.; MacCoss, M.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2002, 12, 611-614.
13. For very recent examples of bioactive peptidomimetics containing α-sulfonylamino amide moieties, see: (a) Das, J. Kimball, S. D.; Reid, J. A.; Wang, T. C.; Lau, W. F. Roberts, D. G. M.; Seiler, S. M.; Schumacher, W. A.; Ogletree, M. L. Bioorg. Med. Chem. Lett. 2002, 12, 41-44; (b) Lin, L. S.; Kopka, I. E.; Mumford, R. A.; Magriotis, P. A.; Lanza, T., Jr.; Durette, P. L.; Kamenecka, T.; Young, D. N.; de Laszlo, S. E.; McCauley, E.; Van Riper, G.; Kidambi, U.; Egger, L. A.; Tong, X.; Lyons, K.; Vincent, S.; Stearns, R.; Colletti, A.; Teffera, Y.; Fenyk-Melody, J.; Schmidt, J. A.; MacCoss, M.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2002, 12, 611-614.
14. Advanced ChemTech, Louisville, KY (800) 456-1403.
15. 3OD): 4a: δ 7.94-8.11 (m, 4H), 7.10-7.32 (m, 5H), 3.78-3.85 (m, 1H), 2.73 (m, 1H), 2.61 (m, 1H), 1.94 (m, 1H), 1.86 (m, 1H), 1.15 (s, 9H). 4h: δ 8.00 (d, J=8.5 Hz, 2H), 7.86 (d, J=8.5 Hz, 2H), 7.09-7.24 (m, 5H), 3.75-3.77 (dd, 1H), 3.28 (m, 1H), 2.63-2.68 (m, 1H), 2.49-2.55 (m, 1H), 0.90-1.90 (m, 12H). 4i: 7.98 (d, J=8 Hz, 2H), 7.91 (d, J=8 Hz, 2H), 7.03-7.27 (m, 10H), 4.16 (d, J=12 Hz, 1H), 4.10 (d, J=12 Hz, 1H), 3.81 (m, 1H), 1.35 (m, 2H), 0.92 (m, 2H).
16. 3OD): δ 8.04 (d, J=7 Hz, 2H), 7.89 (d, J=7 Hz, 2H), 7.11-7.38 (m, 5H), 4.38 (t, 1H), 3.00 (s, 3H), 2.50 (t, 2H), 1.97-2.01 (m, 1H), 1.70-1.74 (m, 1H), 1.21 (s, 9H). 6b: δ 8.00 (d, J=8 Hz, 2H), 7.88 (d, J=8 Hz, 2H), 6.99-7.32 (m, 10H), 4.45-4.53 (dd, J=11.50 Hz, 2H), 4.21-4.24 (m, 1H), 3.80 (m, 1H), 3.68 (m, 2H), 3.53-3.56 (m, 1H), 1H), 2.46 (m, 2H), 2.06 (m, 1H), 1.68 (m, 1H), 1.21 (s, 9H).
17. 3OD): δ 7.53-7.87 (m, 5H), 7.08-7.24 (m, 5H), 3.74 (t, 1H), 2.64 (m, 1H), 2.48 (m, 1H), 1.86 (m, 1H), 1.75 (m, 1H), 1.14 (s, 9H). 8b: δ 8.35-7.13 (m, 9H), 3.894 (m, 1H), 2.64 (m, 1H), 2.69 (t, 2H), 2.01 (m, 1H), 1.82 (m, 1H), 1.75 (m, 1H), 1.36 (s, 9H). 8c: δ 8.08 (d, J=8 Hz, 1H), 7.91 (d, J=8 Hz, 1H), 7.74-7.83 (m, 2H), 7.13-7.25 (m, 5H), 3.92 (m, 1H), 2.71 (m, 1H), 2.58 (m, 1H), 1.95 (m, 1H), 1.88 (m, 1H), 1.11 (s, 9H).