Summary
This review is a historical accounting of chemical libraries from which biologically active agents have been obtained. The comprehensive tabulation includes citations as early as 1992, when the first descriptions of biologically active libraries were disclosed, and continues through 1997. Four tables are provided listing libraries screened against (1) proteolytic enzymes, (2) non-proteolytic enzymes, (3) G-protein coupled receptors (GPCRs), and (4) other targets not classified in the first three tables (e.g., non-GPCRs, integrins, antiinfectives). A name, generic structure, and size is provided for each library citation, accompanied by the molecular screen and the structure and potency of the most active library member. In total, 86 libraries are presented with 60% of the contributions reported from pharmaceutical and biotechnology companies. Approximately 70% of the libraries have used α-amino acid synthons in their construction and 85% of the libraries include one or more amide bonds.
Key words
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
a. Thompson, L.A. and Ellman, J.A., Synthesis and application of small molecule libraries, Chem. Rev., 96 (1996) 555–600.
Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P. and Gordon, E.M., Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries, J. M.d. Chem., 37 (1994) 1233–1251.
Gordon, E.M., Gallop, M.A. and Patel, D.V., Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery, Acc. Chem. Res., 29 (1996) 144–154.
Terrett, N., 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.
Wilson, S.R. and Czarnik, A.W., Combinatorial chemistry. Synthesis and application, John Wiley und Sons, New York, 1997.
Balkenhohl, F., von dem Bussche-Hunefeld, C., Lan-sky, A. and Zechel, C., Combinatorial synthesis of small organic molecules,Angew. Chem. Intl. Ed. Engl., 35 (1996) 228–2337.
Ellman, J.A., Design, synthesis, and evaluation of small-molecule libraries, Acc. Chem. Res., 29 (1996) 132–143.
Hermkens, P.H., Ottenheijm, H.C. and Rees, D.C., Solid-phase organic reactions. II: A review of the literature, Tetrahedron, 53 (1997) 5643–5678.
Hermkens, P.H., Ottenheijm, H.C. and Rees, D.C., Solid-phase organic reactions: A review of the recent literature, Tetrahedron, 52 (1996) 4527–4554.
Flynn, D.L., Crich, J.Z., Devraj, R.V., Hockerman, S.L., Parlow, J.J., South, M.S. and Woodward, S., Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition,J. Am. Chem. Soc., 119 (1997) 4874881.
Parlow, J.J., Naing, W., South, M.S. and Flynn, D.L., In situ chemical tagging: Tetrafluorophthalic anhydride as a ‘Sequestration enabling reagent’ (SER) in the purification of solution-phase combinatorial libraries, Tetrahedron Lett., 38 (1997) 7959–7962.
Dolle, R., Discovery of enzyme inhibitors through combinatorial chemistry, Mol. Div., 2 (1996) 223–236.
Cowley, P.M. and Rees, D., Application of solid-phase synthesis to drug discovery, Curr. Med. Chem., 4 (1997) 211–227.
Bastos, M., Maeji, N.J. and Abeles, R.H., Inhibitors of human heart chymase based on a peptide library, Proc. Natl. Acad. Sci. USA, 92 (1995) 6738–6742.
Campbell, D.A., Bermak, J.C., Burkoth, T.S. and Patel, D.V., A transition state analogue inhibitor combinatorial library, J. Am. Chem. Soc., 117 (1995) 5381–5382.
Carell, T., Wintner, E.A., Sutherland, A.J., Rebek, J., Jr., Dunayevskiy, Y.M. and Vouros, P., New promise in combinatorial chemistry: synthesis, characterization, and screening of small-molecule libraries in solution, Chem. Biol., 2 (1995) 171–183.
a. Chen, C.L., Strop, P., Lebl, M. and Lam, K.S., One bead-one compound combinatorial peptide library: Different types of screening, Combinatorial Chem., 267 (1996) 211–219.
Seligman, B., Abdul-Latif, E, Al-Obeidi, F., Flegelova, Z., Issakova, O., Kocis, P., Krchnak, V., Lam, K.S., Lebl, M., Ostrem, J., Safar, P., Sepetov, N., Stierandova, A., Strop, P. and Wildgoose, P., The construction and use of peptide and nonpeptidic combinatorial libraries to discover enzyme inhibitors, Eur. J. Med. Chem. 30 (supplement) (1995) 319s - 335s.
Kocis, P., Issakova, I., Sepetov, N.F. and Lebl, M., Kemp’s triacid scaffolding for synthesis of combinatorial nonpeptide uncoded libraries, Tetrahedron Lett., 37 (1995) 6623–6626.
a. Eichler, J. and Houghten, R.A., Identification of substrate-analog trypsin inhibitors through the screening of synthetic peptide combinatorial libraries, Biochemistry, 32 (1993) 11035–11041.
Coombs, G.S., Hazzard, J. and Corey, D.R., Kinetic characterization of a peptide inhibitor of trypsin isolated from a synthetic peptide combinatorial library, Bioorg. Med. Chem. Lett., 5 (1995) 611–6614.
Pinilla, C., Appel, J.R., Blondell, S.E., Dooley, C.T., Eichler, J., Ostresh, J.M. and Houghten, R.A., Versatility of positional scanning synthetic combinatorial libraries for the identification of individual compounds, Drug Dev. Res., 33 (1994) 133–145.
Pinilla, C., Appel, J.R., Blondell, S.E., Dooley, C.T., Domer, B., Eichler, J., Ostresh, J. and Houghten, R.A., A review of the utility of soluble peptide combinatorial libraries, Biopolymers (Pep. Sci.) 37 (1995) 221–240.
Eichler, J., Lucka, A.W. and Houghten, R.A., Cyclic peptide template combinatorial libraries: Synthesis and identification of chymotrypsin inhibitors, Peptide Res., 7 (1994) 300–307.
Esser, C.K., Kevin, N.J., Yates, N.A. and Chapman, K.T., Solid-phase synthesis of a N-carboxyalkyl tripeptide combinatorial library, Bioorg. Med. Chem. Lett., 20 (1997) 2639–2644.
Ferry, G., Boutin, J.A., Atassi, G., Fauchere, J.L. and Tucker, G.C., Selection of a histidine-containing inhibitor of gelati-nases through deconvolution of combinatorial tetrapeptide libraries, Mol. Div., 2 (1996) 135–146.
Foley, M.A., Hassman, A.S., Drewry, D.H., Greer, D.G., Wagner, C.D., Feldman, P.L., Berman, J., Bickett, D.M., McGeeham, G.M., Lambert, M.H., and Green, M., Rapid synthesis of novel dipeptide inhibitors of human collagenase and gelatinase using solid phase chemistry, Bioorg. M.d. Chem. Lett., 6 (1996) 1905–1910.
Jiracek, J., Yiotakis, A. Vincent, B., Checler, F. and Dive, V., Development of the first potent and selective inhibitor of the zinc endopeptidase neurolysin using a systematic approach based on combinatorial chemistry of phosphinic peptides, J. B.ol. Chem., 271 (1996) 19606–19611.
Jiracek, J., Yiotakis, A., Vincent, B., Lecoq, A., Nicolaou A., Checler, F. and Dive, V., Development of highly potent and selective phosphinic peptide inhibitors of zinc endopeptidase 24–15 using combinatorial chemistry, J. Biol. Chem., 270 (1995) 21701–21706.
Kick, E.K. and Ellman, J.A., Expedient method for the solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries, J. Med. Chem., 38 (1995) 1427–1430.
Kick, E.K., Roe, D.C., Skillman, A.G., Liu, G., Ewing, T.J.A., Sun, Y., Kuntz, I.D. and Ellman, J.A., Structure-based design and combinatorial chemistry yield low nanomolar inhibitors of cathepsin D, Chem. Biol., 4 (1997) 297–307.
Lloyd, J., Schmidt, J.B., Hunt, J.T., Barrish, J.C., Little, D.K. and Tymiak, A.A., Solid phase synthesis of phosphinic acid endothelin converting enzyme inhibitors, Bioorg. Med. Chem. Lett., 6 (1996) 1323–1326.
McBride, J.D., Freeman, N., Domingo, G.J. and Leatherbarrow, R.J., Selection of chymotrypsin inhibitors from a conformationally-constrained combinatorial peptide library, J. Mol. Biol., 259 (1996) 819–827.
Maclean, D., Schullek, J.R., Murphy, M.M., Ni, Z.J., Gordon, E.M. and Gallop, M.A., Encoded combinatorial chemistry: Synthesis and screening of a library of highly functionalized pyrrolidines, Proc. Natl. Acad. Sci. USA, 94 (1997) 2805–2810.
Meldal, M. and Svendsen, I., Direct visualization of enzyme inhibitors using a portion mixing inhibitor library containing a quenched, luorogenic peptide substrate. Part 1. Inhibitors for subtilisin carlsberg, J. Chem. Soc., Perkin Trans. 1, 12 (1995) 1591–1596.
Murphy, M.M., Schullek, J.R., Gordon, E.M. and Gallop, M.A., Combinatorial organic synthesis of highly functionalized pyrrolidines: Identification of a potent angiotensin converting enzyme inhibitor from a mercaptoacyl proline library, J. Am. Chem. Soc., 117 (1995) 7029–7030.
Owens, R.A., Gesellchen, P.D., Houchins, B.J. and Di-Marchi, R.D., The rapid identification of HIV protease inhibitors through the synthesis and screening of defined peptide mixtures, Biochem. Biophys. Res. Commun., 181 (1991) 402–408.
a. Rano, T.A., T.mkey, T., Peterson, E.P., Rotonda, J., Nicholson, D.W., Becker, J.W., Chapman, K.T. and Thomberry, N.A., A combinatorial approach for determining protease specificities: Application to interleukin-lß converting enzyme (ICE), Chem. Biol., 4 (1997) 149–155.
Thornberry, N.A., Rano, T.A., Peterson, E.P., Rasper, D.M., Timkey T., Garcia-Calvo, M., Houtzager, V.M., Nordstrom, P.A., Roy, S., Vaillancourt, J.P., Chapman, K.T. and Nicholson, D.W., A combinatorial approach defines specificities of members of the caspase family and granzyme B, J. Biol. Chem., 29 (1997) 17907–17911.
Rockwell, A., Melden, M., Copeland, R.A., Hardman, K., Decicco, C.P. and DeGrado, W.F., Complementarily of combinatorial chemistry and structure-based ligand design: application to the discovery of novel inhibitors of matrix metalloproteinases, J. Am. Chem. Soc., 118 (1996) 10337–10338.
Rutenber, E.E., McPhee, F., Kaplan, A.P., Gallion, S.L., Hogan, J.C., Jr., Craik, C.S. and Stroud, R.M., A New class of HIV-1 protease inhibitors: The crystallographic structure, inhibition and chemical synthesis of an aminimide peptide isostere, Bioorg. Med. Chem. Lett., 4 (1996) 1545–1558.
Schullek, J.R., Butler, J.H., Ni, Z.J., Chen, D. and Yuan, Z., A high-density screening format for encoded combinatorial libraries: Assay miniaturization and its application to enzymatic reactions, Anal. Biochem., 246 (1997) 20–29.
Simon, R.J., Kania, R.S., Zuckermann, R.N., Huebner, V.D., Jewell, D.A., Banville, S., Ng, S., Wang, L., Rosenberg, S., Marlowe, C.K., Spellmeyer, D.C., Tan, R., Frankel A.D., Santi, D.V., Cohen, F.E. and Bartlett, P.A., Peptoids: A modular approach to drug discovery, Proc. Natl. Acad. Sci. USA, 89 (1992) 9367–9371.
Wang, G.T., Li, S., Wideburg, N., Krafft, G.A. and Kempf, D.J., Synthetic chemical diversity: Solid phase synthesis of libraries of C(2) symmetric inhibitors of HIV protease containing diamino diol and diamino alcohols cores, J. Med. Chem., 38 (1995) 2995–3002.
a. Chabala, J.C., Baldwin, J.J., Burbaum, J.J., Chelsky, D., Dillard, L.W., Henderson, I., Li, G., Ohlmeyer, M.H.J., Randle, T.L., Reader, J.C., Rokosz, L. and Sigal, N.H., Binary encoded small-molecular libraries in drug discovery and optimization, Perspectives in Drug Discovery Design, 2 (1994) 305–318.
Baldwin, J. J., Burbaum, J.J., Henderson, I. and Ohlmeyer, M.H., Synthesis of a small molecule combinatorial library encoded with molecular tags, J. Am. Chem. Soc., 117 (1995) 5588–5589.
Barbaum, J.J., Ohlmeyer, M.H.J., Reader, J.C., Henderson, I., Dillard, L.W., Li, G., Randle, T.L., Sigal, N.H., Chelsky, D. and Baldwin, J.J., A pardigm for drug discovery employing encoded combinatorial libraries, Proc. Natl. Acad. Sci. USA, 92 (1995) 6027–6031.
Davis, P.W., Vickers, T., Wilson-Lingardo, L., Wyatt, J.R., Guinosso, C.J., Sanghvi, Y.S., DeBaets, E.A., Acevedo, O., Cook, P.D. and Ecker, D.J., Drug leads from combinatorial phosphodiester libraries, J. Med. Chem., 38 (1995) 4363–4366.
Eichler, J., Lucka, A.W., Pinilla, C. and Houghten, R.A., Novel a-glucosidase inhibitors identified using multiple cyclic peptide combinatorial libraries, Mol. Div., 1 (1995) 233–240.
Gao, J., Cheng, R.C., Sigal, G.B., Bruce, J.E., Schwartz, B.L., Hofstadler, S.A., Anderson, G.A., Smith, R.D. and Whitesides, G.M., Screening derivatized peptide libraries for tight binding inhibitors to carbonic anhydrase II by electrospray ionization-mass spectrometry, J. Med. Chem., 39 (1996) 1949–1955.
Green, J., Solid Phase Synthesis of Lavendustin A and Analogues, J. Org. Chem., 60 (1995) 4287–4290.
Lingardo, L.W., Davis, P.W., Ecker, D.J., Herbert, N., Acevedo, O., Sprankle, K., Brennan, T., Schwarcz, L., Freier, S.M. and Wyatt, J.R., Decovolution of combinatorial libraries for drug discovery: experimental comparison of pooling strategies, J. Med. Chem., 39 (1996) 2720–2726.
Look, G.C., Schullek, J.R., Holmes, C.P., Chinn, J.P., Gordon, E.M. and Gallop, M.A., The identification of cyclooxygenase1 inhibitors from 4-thiazolidinone combinatorial libraries, Bioorg. M.d. Chem. Lett., 6 (1996) 707–712.
Lutzke, R.A.P., Eppens, N.A., Weber, P.A., Houghten, R.A. and Plasterk, R.H.A., Identification of a hexapeptide inhibitor of the human immunodeficiency virus integrase protein by using a combinatorial chemical library, Proc. Natl. Acad. Sci. USA, 92 (1995) 11456–11460.
Meyers, H.V., Dilley, G.J., Durgin, T.L., Powers, T.S., Winssinger, N.A., Zhu, H. and Pavia, M.R., Multiple simultaneous synthesis of phenolic libraries, Mol. Div., 1 (1995) 13–20.
Moran, E.J., Sarshar, S., Cargill, J.F., Shahbaz, M.M., Lio, A., Mjalli, A.M. and Armstrong, R.W., Radio frequency tag encoded combinatorial library method for the discovery of tripeptide-substituted cinnamic acid inhibitors of the protein tyrosine phosphotase PTPIB, J. Am. Chem. Soc., 117 (1995) 10787–10788.
Norman, T.C., Gray, N.S., Koh, J.T. and Schultz, P.G., A structure-based library approach to kinase inhibitors, J. Am. Chem. Soc., 118 (1996) 7430–7431.
Samson, I., Kerremans, L., Rozenski, J., Samyn, B., Van Beeumen, J., Van Aerschot A. and Herdewijn, P., Identification of a peptide inhibitor against glycosomal phosphoglycerate kinase of Trypanosoma brucei by a synthetic peptide library approach, Bioorg. Med. Chem. Lett., 3 (1995) 257–265.
Samson, I., K., Rozenski, J., Samyn, B., Van Aerschot A., Van Beeumen, J. and Herdewijn, P., Screening a random pentapeptide library, composed of 14 D-amino acids, against the COOH-terminal sequence offructose-1,6-bisphosphate aldolase from Trypanosoma brucei, J. Biol. Chem., 272 (1997) 11378–11383.
Selway, C.N. and Terrett, N.K., Parallel-compound synthesis: Methodology for accelerating drug discovery, Bioorg. Med. Chem., 4 (1996) 645–654.
Wallace, A., Koblan, K.S., Hamilton, K., Marquis-Omer, D.J., Miller, P.J., Mosser, S.D., Omer, C.A., Schaber, M.D., Cortese, R., Oliff, A., Gibbs, J.B. and Pessi, A., Selection of potent inhibitors of farnesyl-protein transferase from a synthetic tetrapeptide combinatorial library, J. Biol. Chem., 271 (1996) 31306–31311.
Wipf, P., Cunningham, A., Rice, R.L. and Lazo, J.S., Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors, Bioorg. Med. Chem., 5 (1997) 165–177.
Zhao, Y.Z., Van Breemen, R.B., Nikolic, D., Huang, C.R., Woodbury, C.P., Schilling, A. and Venton, D.L., Screening solution-phase combinatorial libraries using pulsed ultrafiltration/electrospray mass spectrometry, J. Med. Chem., 40 (1997) 4006–4012.
Bitan, G., Sukhohotinsky, I., Mashriki, Y., Hanaini, M., Selinger, Z. and Gilon, C., Synthesis and biological activity of novel backbone-bicyclic substance-P analogs containing lactam and disulfide bridges, J. Pept. Res., 49 (1997) 421–426.
Boden, P., Eden, J.M., Hodgson, J., Horwell, D.C., Howson, W., Hughes, J., McKnight, A.T., Meecham, K., Pritchard, M.C., Raphy, J., Ratcliffe, G.S., Suman-Chauhan, N.S. and Woodruff, G.N., The rational development of small molecule tachykinin NK3 receptor selective antagonists-the utilization of a dipeptide chemical library in drug design, Bioorg. Med. Chem. Lett., 4 (1994) 1679–1684.
Bunin, B., Plunkett, M. and Ellman, J., The combinatorial synthesis and chemical and biological evaluation of a 1,4benzodiazepine library, Proc. Natl. Acad. Sci. USA, 91 (1994) 4708–4712.
Chakravarty, S., Mavunkel, B.J., Goehring, R.R. and Kyle, D.J., Novel bradykinin receptor antagonists from a structurally directed non-peptide combinatorial library, Immunopharm., 33 (1996) 61–67.
a. Chen, C., Dagnino, R., Jr., De Souza, E.B., Grigoriadis, D.E., Huang, C.Q., Kim, K.I., Liu, Z., Moran, T., Webb, T.R., Whitten, J.P., Xie, Y.F. and McCarthy, J.R., Design and synthesis of a series of non peptide high-affinity human corticotropin-releasing factor“ receptor antagonists, J. Med. Chem., 39 (1996) 4358–4360.
Whitten, J.P., Xie, Y.F., Erickson, P.E., Webb, T.R., De Souza, E.B., Grigoriadis, D.E. and McCarthy, J.R., Rapid microscale synthesis, a new method for lead optimization using mbotics and solution phase chemistry: Application to the synthesis and optimization of corticotropin-releasing factor“ receptor antagonists, J. Med. Chem., 39 (1996) 4354–4357.
Deprez, B., Willard, X., Bourel, L., Coste, H., Hyafil, F. and Tartar, A., Orthogonal Combinatorial Libraries, J. A.. Chem. Soc., 117 (1995) 5405–5406.
Dooley, C.T., Chung, N.N., Schiller, P.W. and Houghten, R.A., Acetalins: Opioid receptor antagonists determined through the use of synthetic peptide combinatorial libraries, Proc. Natl. Acad. Sci. USA, 90 (1993) 10811–10815.
Dooley, C.T., Chung, N.N., Wilkes, B.C., Schiller, P.W., Bidlack, J.M., Pastmack, G.W. and Houghten, R.A., An all D-amino opioid peptide with central analgesic activity from a combinatorial library, Science, 266 (1994) 2019–2022.
a. Dooley, C. and Houghten, R., The use of positional scanning synthetic peptide combinatorial libraries for the rapid determination of opioid receptor ligands, Life Sci., 52 (1993) 1509–1517.
Houghten, R. and Dooley, C., The use of synthetic peptide combinatorial libraries for the determination of peptide ligands in radio-receptor assays: Opioid peptides, Bioorg. Med. Chem. Lett., 3 (1993) 405–412.
Dooley, C.,Prochera, A.M. and Houghten, R.A., A priori determination of peptide ligands for opiate receptors using synthetic peptide combinatorial libraries,Peptides, (1992) 649–650.
Dooley, C.T., Kaplan, R.A., Schiller, P.W., Bidlack, J.M. and Houghten, R.A., Six highly active Mu-selective opioid peptides identified from two synthetic combinatorial libraries, Pep. Res., 3 (1995) 124–137.
Drouillant, B., Kellam, B., Dekany, G., Starr, M.S. and Toth, I., Solid phase synthesis of C-terminal carbohydrate modified enkephalins, Bioorg. Med. Chem. Lett., 7 (1997) 2247–2250.
Heizmann, G., Tanner, H. and Eberle, A.N., New ligands for the human melanoma MSH receptor identified by a peptoid library (oligo n-substituted glycines), Innovation Perspect. Solid Phase Synth. Comb. Libr. Collect. Pap., 4th International Symposium, Meeting Date 1995, 391–394.
Hirshmann, R., Yao, W., Cascieri, M., Strader, C., Maechler, L., Cichy-Knight, M., Hynes, J.,Jr., van Rijn, R., Spengeler, P. and Smith, A., Synthesis of potent cyclic hexapeptide NK-1 antagonists. Use of a minilibrary in transforming a peptidal somatostatin receptor ligand into an NK-1 receptor ligand via a polyvalent peptidomimetic,J. Med. Chem., 39 (1996) 24412448.
a. Horwell, D.C., Howson, W., Ratcliffe, G.S., and Rees, D.C.,The design of a dipeptide library for screening at peptide receptor sites, Bioorg. Med. Chem. Lett., 3 (1993) 799–802. b. Horwell, D.C., Pritchard, M., Raphy, J. and Ratcliffe, G.S., Targeted molecular diversity: Design and development of non-peptide antagonists for cholecystokinin and tachykinin receptors, Immunopharm., 33 (1996) 68–72.
a. Maher, H. and Yang, R., Structure optimization of a leukotriene D4 antagonist by combinatorial chemistry in solution, Bioorg. Med. Chem. Lett., 5 (1997) 493–496.
O’Donnell, M., Crowley, H.J., Yaremko, B., O’Neill, N. and Welton, A.F., Pharmacologic actions of Ro 24–5913, a novel antagonist of leukotriene D4, J. Pharm. Exp. Ther., 259 (1991) 751–758.
Neustadt, B., Wu, A., Smith, E.M., Nechuta, T., Fawzi, A., Zhang, H. and Ganguly, A.K., A case study of combinatorial libraries: Endothelin receptor antagonist hexapeptides, Bioorg. Med. Chem. Lett., 5 (1995) 2041–2044.
Quillian, J.M., Jayawickreme, C.K. and Lerner, M.R., Combinatorial diffusion assay used to identify topically active melanocyte-stimulating hormone receptor antagonists, Proc. Natl. Acad. Sci. USA, 92 (1995) 2894–2898.
Spellmeyer, D.C, Brown, S. and Stauber, G., Endothelin receptor ligands. Replacement net approach to SAR determination potent hexapeptides, Bioorg. Med. Chem. Lett., 3 (1993) 519–524.
Spellmeyer, D.C., Brown, S. and Stauber, G., Endothelin receptor ligands. Multiple D-amino acid replacement net approach, Bioorg. Med. Chem. Lett., 3 (1993) 1253–1256.
Terrett, N.K., Bojanic, D., Brown, D., Bungay, P., Gardner, M., Gordon, D.W., Mayers, C.J. and Steele, J.,The combinatorial synthesis of a 30,752-compound library: Discovery of SAR around the endothelin antagonist, FR-139, 317. Bioorg. Med. Chem. Lett., 5 (1995) 917–922.
Terrett, N.K., Gardner, M., Gordon, D.W., Kobylecki, R.J. and Steele, J., Drug discovery by combinatorial chemistry-The development of a novel method for the rapid synthesis of single compounds, J. Eur. Chem., 3 (1997) 1917–1920.
a. Wang, J.X., Bray, A.M., DiPasquale, A.J., Maeji, N.J. and Geysen, H.M., Systematic study of substance P analogs: Evaluation of peptides synthesized by the multipin method for quantitative receptor binding assay, Int. J. Peptide Protein Res., 42 (1993) 384–391.
Wang, J.X., DiPasquale, A.J., Bray, A.M., Maeji, N.J. and Geysen, H.M., Study of stereo-requirements of substance P binding to NK1 receptors using analogues with systematic d-amino acid replacements, Bioorg. Med. Chem. Lett., 13 (1993) 451–456.
Wang, J.X., Bray, A.M., DiPasquale, A.J., Maeji, N.J. and Geysen, H.M., Application of the multipin peptide synthesis technique for peptide receptor binding studies: Substance P as a model system, Bioorg. Med. Chem. Lett., 3 (1993) 447–450.
Zuckerman, R.N., Martin, E.J., Spellmeyer, D.C., Stauber, G.B., Shoemaker, K.R., Kerr, J.M., Figliozzi, G.M., Goff, D.A., Siani, D., Simon, R., Banville, S.C., Brown, E.G., Wang, L., Richter, L.S. and Moos, W., Discovery of nanomolar ligands for 7-transmembrane G-protein-coupled receptors from a diverse N-(substituted) glycine peptoid library, J. Med. Chem. 37 (1994) 2678–2685.
Virgilio, A.A., Bray, A.A., Zhang, W., Trinh, L., Snyder, M., Morrissey, M.M. and Ellman, J.A., Synthesis and eval- uation of a library of peptidomimetics based upon the B-turn, Tetrahedron, 53 (1997) 6635–6644.
Williard, R., Jammalamadaka, V., Zava, D., Bens, C.C., Hunt, C.A., Kushner, P.J. and Scanlan, T.S., Screening and characterization of estrogenic activity from a hydmxystilbene library, Chem. Biol., 2 (1995) 45–51.
An, H., Cummins, L.L., Griffey, R.H., Bharadwaj, R., Haly, B.D., Fraser, A.S., Wilson-Lingardo, L., Risen, L.M., Wyatt, J.R. and Cook, P.D., Solution phase combinatorial chemistry: Discovery of novel polyazapyridinophanes with potent antibacterial activity by a solution phase simultaneous addition of functionalities approach, J. Am. Chem. Soc., 119 (1997) 3696–3708.
An, H., Haly, B.D., Fraser, A.S., Guinosso, C.J. and Cook, P.D., Solution phase combinatorial chemistry. Synthesis of novel linear pyridinopolyamine libraries with potent antibacterial activity, J. Org. Chem., 62 (1997) 5156–5164.
Corbett, J.W., Graciani, N.R., Mousa, S.A. and DeGrado, W.E., Solid-phase synthesis of a selective avß3 integrin antagonist library, Bioorg. Med. Chem. Lett., 7 (1997) 13711376.
Hajduk, P.J., Dinges, J., Miknis, G.F., Merlock, M., Middleton, T., Kempf, D.J., Egan, D.A., Walter, K.A., Robins, T.S., Shuker, S.B., Holzman, T.F. and Fesik, E., NMR-based discovery of lead inhibitors that block DNA binding of the human papillomavirus E2 protein, J. Med. Chem., 40 (1997) 3144–3150.
Harada, T., Katada, J., Tachiki, A., Asari, T., Iijima, K., Uno, I., Ojima, I. and Hayashi, Y., Development of the new potent non-peptide GpIIb/IIIa antagonist NSL-95301 by utilizing combinatorial technique, Bioorg. Med. Chem. Lett., 7 (1997) 209–212.
Kaldor, S., Fritz, J.E., Tang, J. and McKinney, E.R., Discovery of antirhinoviral leads by screening a combinatorial library of ureas prepared using covalent scavengers, Bioorg. Med. Chem. Lett., 6 (1996) 3041–3044.
Koppel, G., Dodds, C., Houchins, B., Hunden, D., Johnson, D., Owens, R., Chaney, M., Usdin, T., Hoffman, B. and Brownstein, M., Use of peptide combinatorial libraries in drug design: The indication of a potent serotonin reuptake inhibitor derived from a tripeptide cassette library, Chem. Biol., 2 (1995) 483–487.
Park, W.C., Auer, M., Jaksche, H. and Wong, C.H., Rapid combinatorial synthesis of amino glycoside antibiotic mimet-ics: Use of a polythylene glycol-linked amine and a neaminederived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA rev responsive element, J. Am. Chem. Soc., 118 (1996) 10150–10155.
Reed, J.D., Edwards, D.L. and Gonzalez, C.F., Synthetic peptide combinatorial libraries: A method for the identification of bioactive peptides against phytopathogenic fungi, Am. Path. Soc. 10 (1997) 537–549.
Tomkinson, N.C., Sefler, A.M., Plunket, K.D., Blanchard, S.G., Parks, D.J. and Willson, T.M., Solid-phase synthesis of hybrid thiazolidinedione-fatty acid PPARy ligands, Bioorg. Med. Chem. Lett., 19 (1997) 2491–2496.
Houghten, R.A., Pinilla, C., Blondell, S.E., Appel, J.R., Dooley, C.T. and Cuervo, J.H., Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery, Nature, 354 (1991) 84–86.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Dolle, R.E. (1999). Comprehensive survey of chemical libraries yielding enzyme inhibitors, receptor agonists and antagonists, and other biologically active agents: 1992 through 1997. In: Moos, W.H., Pavia, M.R. (eds) Annual Reports in Combinatorial Chemistry and Molecular Diversity. Annual Reports in Combinatorial Chemistry and Molecular Diversity, vol 2. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0735-0_10
Download citation
DOI: https://doi.org/10.1007/978-94-017-0735-0_10
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-5227-8
Online ISBN: 978-94-017-0735-0
eBook Packages: Springer Book Archive