Combinatorial chemistry on solid support in the search for central nervous system agents

Combinatorial Chemistry and High Throughput Screening

Volumn 12, Issue 7, 2009, Pages 723-739

  Zajdel, Paweł ^a   Pawłowski, Maciej ^a   Martinez, Jean ^b   Subra, Gilles ^b  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; BP 897; BUSPIRONE; CENTRAL NERVOUS SYSTEM AGENTS; DOPAMINE RECEPTOR AFFECTING AGENT; FUNCTIONAL GROUP; HYDANTOIN DERIVATIVE; INDOLE DERIVATIVE; KETANSERIN; MIANSERIN; NEUROKININ 1 RECEPTOR ANTAGONIST; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RESIN; SEROTONIN 2A ANTAGONIST; VOLINANSERIN;

CLINICAL TRIAL; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; DRUG SCREENING; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; HUMAN; NONHUMAN; PRIORITY JOURNAL; REVIEW; SCHIZOPHRENIA; SOLID; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZODIAZEPINES; CENTRAL NERVOUS SYSTEM AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; HUMANS; MOLECULAR STRUCTURE;

EID: 68549117292     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620709788923719     Document Type: Review

References (75)

1. Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.; Gordon, E.M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J. Med. Chem., 1994, 37, 1233-1251
2. Gordon, E.M.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J. Med. Chem., 1994, 37, 1385-1401.
3. Konings, D.A.M.; Wyatt, J.R.; Ecker, D.J.; Freier, S.M. Strategies for rapid deconvolution of combinational libraries: comparative evaluation using a model system. J. Med. Chem., 1997, 40, 4386-4395
4. Jung, G. Combinatorial chemistry: synthesis, analysis, screening; Willey-VCH Verlag: Wenheim, 1999.
5. Déprez, B.; Willard, X.; Bourel, L.; Coste, H.; Hyafil, F.; Tartar, A. Orthogonal combinatorial chemical libraries. J. Am. Chem. Soc., 1995, 117, 5405-5406
6. Furka, A.; Bennett, W.D. Combinatorial libraries by portioning and mixing. Comb. Chem. High Throughput Screen., 1999, 2, 105-122
7. Jayawickreme, C.K.; Sauls, H.; Bolio, N.; Ruan, J.; Moyer, M.; Burkhart, W.; Marron, B.; Rimele, T.; Shaffer, J. Use of a cell-based, lawn format assay to rapidly screen a 442,368 bead-based peptide library. J. Pharmacol. Toxicol. Methods., 1999, 42, 189-197 (Pubitemid 30734393)
8. Marron, B.E.; Jayawickreme, C.K. Going to the well no more: lawn format assays for ultra-high-throughput screening. Curr. Opin. Chem. Biol., 2003, 7, 395-401.
9. Miyashita, M.; Otake, Y.; Oda, M.; Miyagawa, H. Development of a high-throughput screening method using a cell-based, lawn format assay for the identification of novel plant defense activators from combinatorial peptide libraries. J. Agric. Food. Chem., 2007, 55, 806-811
10. Geysen, H.M.; Schoenen, F.; Wagner, D.; Wagner, R. Combinatorial compound libraries for drug discovery: an ongoing challenge. Nat. Rev. Drug. Discov., 2003, 2, 222-230 (Pubitemid 37361667)
11. Aggarwal, S.; Harden, J.L.; Denmeade, S.R. Synthesis and screening of a random dimeric peptide library using the one-bead-one- dimer combinatorial approach. Bioconjug. Chem., 2006, 17, 335-340
12. Camperi, S.A.; Marani, M.M.; Iannucci, N.B.; Cote, S.; Albericio, F.; Cascone, O. An efficient strategy for the preparation of one-bead- one-peptide libraries on a new biocompatible solid support. Tetrahedron Lett., 2005, 46, 1561-1564 (Pubitemid 40215064)
13. www.versamatrix.dk/news/Bioseparation5-2004.pdf
14. Hoffmann, C.; Blechschmidt, D.; Krüger, D.; Karas, M.; Griesinger, C. Mass spectrometric sequencing of individual peptides from combinatorial libraries via specific generation of chain-terminated sequences. J. Comb. Chem., 2002, 4, 79-86.
15. Ede, N.J.; Wu, Z. Beyond Rf tagging. Curr. Opin. Chem. Biol., 2003, 7, 374-379
16. Pirrung, M.C. Spatially addressable combinatorial libraries. Chem. Rev., 1997, 97, 473-488
17. Weller, H.N.; Rubin, A.E.; Moshiri, B.; Ruediger, W.; Li, W.-J.; Allen, J.; Nolfo, J.; Bertok, A.; Rosso, V.W. Development and commercialization of the MiniBlock synthesizer family: a historical case study. J. Assoc. Lab. Autom., 2005, 10, 59-71.
18. Houghten, R.A. General method for the rapid solid-phase synthesis of large numbers of peptides: specificity of antigen-antibody interaction at the level of individual amino acids. Proc. Natl. Acad. Sci. USA, 1985, 82, 5131-5135
19. 2A receptors. J. Comb. Chem., 2004, 6, 761-767
20. Feliu, L.; Subra, G.; Martinez, J.; Amblard, M. Spiroimidazolidinone library derivatives on SynPhase lanterns. J. Comb. Chem., 2003, 5, 356-361 (Pubitemid 37140545)
21. Nicolaou, K.C.; Pfefferkorn, J.A.; Mitchell, H.J.; Roecker, A.J.; Barluenga, S.; Cao, G.-Q.; Affleck, R.L; Lillig, J.E. Natural product-like combinatorial libraries based on privileged structures. 2. Construction of a 10 000-membered benzopyran library by directed split-and-pool chemistry using NanoKans and optical encoding. J. Am. Chem. Soc., 2000, 122, 9954-9967
22. Gerritz, S.W. Whither solid phase synthesis? Curr. Drug Discov., 2002, 6, 19-22.
23. Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. Design and synthesis of a maximally diverse and druglike screening library using REM resin methodology. J. Comb. Chem., 2001, 3, 534-541
24. Lopez-Rodriguez, M.L.; Rosado, M.L.; Benhamu, B.; Morcillo, M.J.; Fernandez, E.; Schaper, K.-J. Synthesis and structure-activity relationships of a new model of arylpiperazines. 2. Three-dimensional quantitative structure-activity relationships of hydantoin-phenylpiperazine derivatives with affinity for 5-HT1A and alpha 1 receptors. A comparison of CoMFA models. J. Med. Chem., 1997, 40, 1648-1656
25. Nowak, M.; Kolaczkowski, M.; Pawlowski, M.; Bojarski, A.J. Homology modeling of the serotonin 5-HT1A receptor using automated docking of bioactive compounds with defined geometry. J. Med. Chem., 2006, 49, 205-214
26. Becker, O.M.; Dhanoa, D.S.; Marantz, Y.; Chen, D.; Shacham, S.; Cheruku, S.; Heifetz, A.; Mohanty, P.; Fichman, M.; Sharadendu, A.; Nudelman, R.; Kauffman, M.; Noiman, S. An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression. J. Med. Chem., 2006, 49, 3116-3135 (Pubitemid 43830511)
27. Kennedy, T. Managing the drug discovery/development interface. Drug Discov. Today., 1997, 2, 436-444
28. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev., 1997, 23, 3-25.
29. Veber, D.F.; Johnson, S.R.; Cheng, H.-Y.; Smith, B.R.; Ward, K.W.; Kopple, K.D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem., 2002, 45, 2615-2623
30. Egan, W.J.; Lauri, G. Prediction of intestinal permeability. Adv. Drug Deliv. Rev., 2002, 54, 273-289
31. Bleicher, K.H.; Bohm, H.-J.; Müller, K.; Alanine, A.I. Hit and lead generation: beyond high-throughput screening. Nat. Rev. Drug Disc., 2003, 2, 369-378 (Pubitemid 37361707)
32. Merrifield R.B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc., 1963, 85, 2149-2154
33. Labadie, J.W. Polymeric supports for solid phase synthesis. Curr. Opin. Chem. Biol., 1998, 2, 346-352 (Pubitemid 128423238)
34. Sherrington, D.C. Preparation, structure and morphology of polymer supports. Chem. Commun., 1998, 21, 2275-2286
35. Czarnik, A.W. Solid-phase synthesis supports are like solvents. Biotechnol. Bioeng., 1998, 61, 77-79 (Pubitemid 28561947)
36. Dolle, R.E. Comprehensive survey of combinatorial library synthesis: 2003. J. Comb. Chem., 2004, 6, 623-679
37. Dolle, R.E.; Le Bourdonnec, B.; Morales, G.A.; Moriarty, K.J.; Salvino, J.M. Comprehensive survey of combinatorial library synthesis: 2005. J. Comb. Chem., 2006, 8, 597-635.
38. Willoughby, C.A.; Berk, S.C.; Rosauer K.G.; Degrado, S.; Chapman, K.T.; Goud, S.L.; Springer, M.S.; Malkowitz, L.; Schleif, W.A.; Hazuda, D.; Miller, M.; Kessler, J. Danzeisen, R.; Holmes, K.; Lineberger, J.; Carella, A.; Carver, G.; Emini, E.A. Combinatorial synthesis of CCR5 antagonists. Bioorg. Med. Chem. Lett., 2001, 11, 3137-3141
39. Choi, C.; Li, J.-H.; Vaal, M.; Thomas, C.; Limburg, D; Wu, Y.-Q.; Chen, Y.; Soni, R.; Scott, C.; Ross, D.T.; Guo, H.; Howorth, P.; Valentine, H.; Liang, S.; Spicer, D.; Fuller, M.; Steiner, J.; Hamilton, G.S. Use of parallel-synthesis combinatorial libraries for rapid identification of potent FKBP12 inhibitors. Bioorg. Med. Chem., Lett., 2002, 12, 1421-1428
40. Nicolaou, K.C.; Roecker, A.J.; Hughes, R.; van Summeren, R.; Pfefferkorn, J.A.; Winssinger, N. Novel strategies for the solid phase synthesis of substituted indolines and indoles. Bioorg. Med. Chem., 2003, 11, 465-476 (Pubitemid 36051037)
41. Severinsen, R.; Lau, J.F.; Bondensgaard, K.; Hansem, B.S.; Begtrup, M.; Ankersen, M. Parallel solid-phase synthesis of disubstituted (5-biphenyltetrazolyl) hydantoins and thiohydantoins targeting the growth hormone secretagogue receptor. Bioorg. Med. Chem., 2004, 14, 317-320 (Pubitemid 38045113)
42. Ho, K.-K.; Appell, K.C.; Baldwin, J.J.; Bohnstedt, A.C.; Dong, G.; Guo, T.; Horlick, R.; Islam, K.R.; Kultgen, S.G.; Masterson, C.M.; MsDonald, E.; McMillan, K.; Morphy, J.R.; Rankovic, Z.; Sundaram, H.; Webb, M. 2-(Aminomethyl)-benzamide-based glycine transporter type-2 inhibitors. Bioorg. Med. Chem. Lett., 2004, 14, 545-548 (Pubitemid 38045164)
43. Ganesan, A. Recent developments in combinatorial organic synthesis. Drug Discov. Today, 2002, 7, 47-55. (Pubitemid 34097451)
44. Bourel-Bonnet, L.; Rao, K.V.; Hamann, M.T.; Ganesan, A. Solid-phase total synthesis of kahalalide A and related analogues. J. Med. Chem., 2005, 48, 1330-1335 (Pubitemid 40364543)
45. Bunin, B.A.; Ellman, J.A. A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives. J. Am. Chem. Soc., 1992, 114, 10997-10998
46. Bhalay, G.; Blaney, P.; Palmer, V.H.; Baxter, A.D. Solid-phase synthesis of diverse tetrahydro-1,4-benzodiazepine-2-ones. Tetrahedron Lett., 1997, 38, 8375-8378
47. Schwartz, M.K.; Tumelty, D.; Gallop, M.A. Solid-phase synthesis of 1,5-benzodiazepin-2-ones. Tetrahedron Lett., 1998, 39, 8397-8400.
48. Boojamra, C.G.; Burow, K.M.; Thompson, L.A.; Ellman, J.A. Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality. J. Org. Chem., 1997, 62, 1240-1256 (Pubitemid 27170232)
49. Nefzi, A.; Ong, N.A.; Giuliatotti, M.A.; Ostresh, J.M.; Houghten, R.A. Solid phase synthesis of 1,4-benzothiazepin-5-one derivatives. Tetrahedron Lett., 1999, 40, 4939-4942 (Pubitemid 29287337)
50. Woolard, F.X.; Paetsch, J.; Ellman, J.A. A silicon linker for direct loading of aromatic compounds to supports. Traceless synthesis of pyridine-based tricyclics. J. Org. Chem., 1997, 2, 6102-6103
51. Smith, A.L.; Stevenson, G.I.; Lewis, S.; Patel, S.; Castro, J.L. Solid-phase synthesis of 2,3-disubstituted indoles: discovery of a novel, high-affinity, selective h5-HT2A antagonist. Bioorg. Med. Chem. Lett., 2000, 10, 2693-2696
52. Stevenson, G.I.; Smith, A.L.; Lewis, S.; Michie, S.G.; Neduvelil, J.G.; Patel, S.; Marwood, R.; Patel, S.; Castro, J.L. 2-Aryl tryptamines: selective high-affinity antagonists for the h5-HT2A receptor. Bioorg. Med. Chem. Lett., 2000, 10, 2697-2699
53. Van Oekelen, D.; Luyten, W.H.; Leysen, J.E. 5-HT2A and 5-HT2C receptors and their atypical regulation properties. Life Sci., 2003, 72, 2429-2449
54. Talvik-Lotfi, M.; Nyberg, S.; Nordstrom, A.-L.; Ito, H.; Halldin, C.; Brunner, F.; Farde, L. High 5HT2A receptor occupancy in M100907-treated schizophrenic patients. Psychopharmacology, 2000, 148, 400-403 (Pubitemid 30169758)
55. Willoughby, C.A.; Hutchins, S.M.; Rosauer, K.G.; Dhar, M.J.; Chapman, K.T.; Chicchi, G.G.; Sadowski, S.; Weinberg, D.H.; Patel, S.; Malkowitz, L.; Di Salvo, J.; Pacholok, S. G.; Cheng, K. Combinatorial synthesis of 3-(amidoalkyl) and 3-(aminoalkyl)-2- arylindole derivatives: discovery of potent ligands for a variety of G-protein coupled receptors. Bioorg. Med. Chem. Lett., 2002, 12, 93-96 (Pubitemid 34008577)
56. Cooper, L.C.; Chicchi, G.G.; Dinnell, K.; Elliot, J.M.; Hollingworth, G.J.; Kurts, M.M.; Locker, K.L.; Morrison, D.; Shaw, D.E.; Tsao, K.-L.; Watt, A.P.; Wiliams, A.R.; Swain, C.J. 2- Aryl indole NK1 receptor antagonists: optimisation of indole substitution. Bioorg. Med. Chem. Lett., 2001, 11, 1233-1236 (Pubitemid 32406092)
57. Bleicher, K.H.; Wüthrich, Y.; De Boni, M.; Kolczewski, S.; Hoffmann, T.; Sleight A.J. Parallel solution- and solid-phase synthesis of spirohydantoin derivatives as neurokinin-1 receptor ligands. Bioorg. Med. Chem. Lett., 2002, 12, 2519-2522 (Pubitemid 35245272)
58. Kelly, J. Novel therapeutic targets for the treatment of depression. Curr. Med. Chem. - Central Nervous Syst. Agents. 2003, 3, 311-322 (Pubitemid 37444240)
59. Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J.M.; Houghten, R.A. Solid-phase synthesis of linear ureas tethered to hydantoins and thiohydantoins. J. Comb. Chem., 2002, 4, 175-178
60. Bettinetti, L.; Löber, S.; Hübner, H.; Gmeiner, P. Parallel synthesis and biological screening of dopamine receptor ligands taking advantage of a click chemistry based BAL linker. J. Comb. Chem., 2005, 7, 309-316 (Pubitemid 40522016)
61. Zhang, A.J.; Russel, D.H.; Zhu, J.; Burgess, K. A method for removal of N-BOC protecting groups from substrates on TFA-sensitive resins. Tetrahedron Lett., 1998, 39, 7439-7442 (Pubitemid 28540826)
62. Wolfe, J.P.; Tomori, H.; Sadighi, J.P.; Yin, J.; Buchwald, S.L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem., 2000, 65, 1158-1174
63. 1A receptor ligands. Bioorg. Med. Chem. Lett., 2006, 16, 3406-3410
64. http://pdsp.med.unc.edu/pdsp.php
65. Guo, T.; Hunter, R.C.; Gu, H.; Rokosz, L.L.; Stauffer, T.; Hobbs, D.W. Discovery and SAR of 4-amino-2-biarylbutylurea MCH 1 receptor antagonists through solid-phase parallel synthesis. Bioorg. Med. Chem. Lett., 2005, 15, 3691-3695 (Pubitemid 41038961)
66. Guo, T.; Shao, Y.; Qian, G.; Rokosz, L.L.; Stauffer, T.M.; Hunter, R.C.; Babu, S.D., Gu, H.; Hobbs, D.W. Discovery and SAR of biaryl piperidine MCH1 receptor antagonists through solid-phase encoded combinatorial synthesis. Bioorg. Med. Chem. Lett., 2005, 15, 3696-3700 (Pubitemid 41038962)
67. Guo, T.; Gu, H.; Hobb, D.W.; Busler, D.E.; Rokosz, L.L. Discovery of tetralin ureas as potent melanin concentrating hormone 1 receptor antagonists. Bioorg. Med. Chem. Lett., 2007, 17, 1718-1721 (Pubitemid 46274335)
68. Baxendale, I.R.; Ernst, M.; Krahnert, W.R.; Ley, S.V. Application of polymer-supported enzymes and reagents in the synthesis of γ- aminobutyric acid (GABA) analogues. Synlett, 2002, 10, 1641-1644
69. Pop, I.E.; Déprez, B.P.; Tartar, A.L. Versatile acylation of N-nucleophiles using a new polymer-supported 1- hydroxybenzotriazole derivative. J. Org. Chem., 1997, 62, 2594-2603 (Pubitemid 127492263)
70. Sumiyoshi, H.; Shimizu, T.; Katoh, M.; Baba, Y.; Sodeoka, M. Solution-phase parallel synthesis of carbamates using polymer-bound N-hydroxysuccinimide. Org. Lett., 2002, 4, 3923-3926
71. Guisado, O.; Martinez, S.; Pastor, J. A novel, facile methodology for the synthesis of N,N′-bis(tert-butoxycarbonyl)-protected guanidines using polymer-supported carbodiimide. Tetrahedron Lett., 2002, 43, 7105-7109 (Pubitemid 35246119)
72. Crosignani, S.; White, P.D.; Linclau, B. Polymer-supported O-methylisourea: A new reagent for the O-methylation of carboxylic acids. Org. Lett., 2002, 4, 1035-1037
73. Habermann, J.; Ley, S.V.; Scott, J.S. Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents. J. Chem. Soc. Perkin Trans. 1, 1998, 3127-3130 (Pubitemid 128765261)
74. Heidler, P.; Zohrabi-Kalantri, V.; Calmels, T.; Capet, M.; Berrebi- Bertrand, I.; Schwartz, J.-C.; Stark, H.; Link, A. Parallel synthesis and dopamine D3/D2 receptor screening of novel {4-[4-(2- methoxyphenyl)piperazin-1- yl]butyl}carboxamides. Bioorg. Med. Chem., 2005, 13, 2009-2014 (Pubitemid 40261122)
75. Burkamp, F; Koon-Fung Cheng, S.; Fletcher S.R. Phenylsulphonylipiperazinyl derivatives as 5-HT receptor ligands. U.S. Patent 6,852,718, February 8, 2005.