Solid phase synthesis of benzamidine-derived sulfonamide libraries

Molecular Diversity

Volumn 3, Issue 2, 1997, Pages 133-136

  Kim, Sang Woong ^a   Hong, Chang Yong ^a   Koh, Jong Sung ^a   Lee, Eun Ju ^b   Lee, Koo ^a  

^a LG Chemical Ltd   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

Benzamidine containing sulfonamide; Solid phase synthesis; Thrombin

Indexed keywords

BENZAMIDINE DERIVATIVE; ENZYME INHIBITOR; PLANT RESIN; SULFONAMIDE; THROMBIN;

ARTICLE; CHEMICAL STRUCTURE; DRUG ANTAGONISM; SYNTHESIS;

BENZAMIDINES; ENZYME INHIBITORS; MOLECULAR STRUCTURE; RESINS, PLANT; SULFONAMIDES; THROMBIN;

EID: 0031995307     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1009608400697     Document Type: Article

References (10)

1. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
2. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
3. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
4. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
5. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
6. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
7. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
8. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
9. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.
10. For recent reviews see: a. Lam, K.S., Lebl, M. and Krchnak, V., The 'one-bead-one-compound' combinatorial library method, Chem. Rev., 97 (1997) 411-448. b. Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gordon, E.M., Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. Med. Chem., 37 (1994) 1233-1251. c. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555-600. d. Nefzi, A., Ostresh, J.M. and Houghten, R.A., The current status of heterocyclic combinatorial libraries, Chem. Rev., 97 (1997) 449-472. e. Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A. and Gallop, M.A., Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and fucture directions, J. Med. Chem., 37 (1994) 1385-1401. f. Desai, M.C., Zuckermann, R.N. and Moos, W.H., Recent advances in the generation of chemical diversity libraries, Drug Dev. Res., 33 (1994) 174-188. g. Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Combinatorial synthesis - the design of compound libraries and their application to drug discovery, Tetrahedron, 51 (1995) 8135-8173. h. Balkenhohl, F., Bussche-Hunnefeld, C.V.D., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2288-2337. Still, W.C., Discovery of sequence-selective peptide binding by synthesis receptors using encoded combinatorial libraries, Acc. Chem. Res., 29 (1996) 155-163. j. Jung, G. and Beck-Sickinger, A.G., Multiple peptide synthesis methods and their applications, Angew. Chem. Int. Ed. Engl., 1992, 31, 367-383.