Combinatorial synthetic design

Current Opinion in Chemical Biology

Volumn 3, Issue 3, 1999, Pages 299-306

  Oliver, Steven F ^a   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; OXAZOLIDINONE DERIVATIVE; PEPTIDE LIBRARY; TETRAHYDROFURAN;

DRUG DESIGN; DRUG SYNTHESIS; METHODOLOGY; REVIEW;

EID: 0033153449     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(99)80046-5     Document Type: Article

References (38)

1. Hollis-Showalter HD: A silicon-based linker for traceless solid-phase synthesis/protodetachable arylsilane polymer linkages for use in solid-phase organic synthesis. Chemtracts - Org Chem 1996, 9:231-236.
2. Piscopio AD, Miller JF, Koch K: A second generation solid phase approach to Freidinger lactams: Application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis. Tetrahedron Lett 1998, 39:2667-2670.
3. Nicolaou KC, Winssinger N, Pastor J, Murphy F: Solid-phase synthesis of macrocyclic systems by a cyclerelease strategy: Application of the Stille coupling to a synthesis of (S)-zearalenone. Angew Chem Int Ed Engl 1998, 37:2534-2537. Solid-phase natural product synthesis is described showing the versatility of the new linker when exposed to a range of conditions.
4. Nicolaou KC, Pastor J, Winssinger N, Murphy F: Solid phase synthesis of macrocycles by an intramolecular ketophosphonate reaction. Synthesis of a (DL)-muscone library. J Am Chem Soc 1998, 120:5132-5133
5. Gong YD, Najdi S, Olmstead MM, Kurth MJ: Solid-phase synthesis: Intramolecular azomethine ylide cycloaddition (→ proline) and carbanilide cyclization (→ hydantoin) reactions. J Org Chem 1998, 63:3081-3086.
6. Stadlwieser J, Ellmerer-Muller EP, Tako A, Maslouh N, Bannwarth W: Combinatorial solid-phase synthesis of structurally complex thiazolylhydantoines. Angew Chem Int Ed Engl 1998, 37:1402-1404.
7. Fantauzzi PP, Yager KM: Synthesis of diverse tetrahydro-beta-carboline-3-carboxamides and 2,3-bis-lactams on a versatile 4-hydroxythiophenol-linked solid support. Tetrahedron Lett 1998, 39:1291-1294.
8. Buchstaller HP: Solid phase synthesis of oxazolidinones via a novel cyclisation/cleavage reaction. Tetrahedron 1998, 54:3465-3470. The principle of this cleavage mechanism, which allows the introduction of diversity, cyclisation and cleavage in tandem, has scope for extension to a number of small cyclic molecules.
9. Sabatino G, Chelli M, Mazzucco S, Ginanneschi M, Papini A-M: Cyclisation of histidine containing peptides in the solid-phase by anchoring the imidazole ring to trityl resins. Tetrahedron Lett 1999, 40:809-812.
10. Jensen KJ, Alsina J, Songster MF, Vagner J, Albericio F, Barany G: Backbone amide linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides. J Am Chem Soc 1998, 120:5441-5452. This paper describes an important advance, which for the first time allows easy access to carboxy-terminal functionalised and cyclic peptides, using well-established chemistry.
11. Cho CY, Youngquist RS, Paikoff SJ, Beresini MH, Hebert AR, Berleau LT, Liu CW, Wemmer DE, Keough T, Schultz PG: Synthesis and screening of linear and cyclic oligocarbamate libraries. Discovery of high affinity ligands for GPIIb/IIIa. J Am Chem Soc 1998, 120:7706-7718. A complete strategy for the assembly of these complex oligomers is described. This is an excellent example of how combinatorial chemistry can impact directly on the drug discovery process.
12. Lin PS, Ganesan A: Solid-phase synthesis of peptidomimetic oligomers with a phosphodiester backbone. Bioorg Med Chem Lett 1998, 8:511-514.
13. Gennari C, Longari C, Ressel S, Salom B, Piarulli U, Ceccarelli S, Mielgo A: Synthesis of combinatorial libraries of vinylogous sulfonamidopeptides (vs-peptides). Eur J Org Chem 1998, 2437-2449.
14. Hamper BC, Kolodziej SA, Scales AM, Smith RG, Cortez E: Solid phase synthesis of beta-peptoids: N-substituted beta-aminopropionic acid oligomers. J Org Chem 1998, 63:708-718. An efficient route to peptidomimetic oligomers from the simplest of starting materials is described.
15. Booth S, Hermkens PHH, Ottenheijm HCJ, Rees DC: Solid-phase organic reactions III: A review of the literature Nov 96-Dec 97. Tetrahedron 1998, 54:15385-15443. This is the third report of its type, which documents the chemical transformations carried out on the solid phase in the said period. Transformations are arranged by reaction type in tabular form.
16. Andres CJ, Whitehouse DL, Deshpande MS: Transition-metal mediated reactions in combinatorial synthesis. Curr Opin Chem Biol 1998, 2:353-362. This is a comprehensive review of recent solid-phase chemistry involving transition metals.
17. Heerding DA, Takata DT, Kwon C, Huffman WF, Samanen J: Combinatorial chemistry. Use of an intramolecular ruthenium catalyzed olefin/alkyne metathesis reaction in tandem with a Diels-Alder cycloaddition reaction to construct functionalized hexahydroisoindoles. Tetrahedron Lett 1998, 39:6815-6818. This paper reports a high-yielding procedure for the production of complex tricyclic moieties using highly efficient sequential C-C bond-forming chemistry and illustrates the importance of diene synthesis on the solid phase.
18. Schurer SC, Blechert S: Ruthenium-catalyzed yne-ene cross metathesis binding to solid support and cleavage by Pd-0-catalysis. Synlett 1998:166-169.
19. Boymond L, Rottlander M, Cahiez G, Knochel P: Preparation of highly functionalized Grignard reagents by an iodine-magnesium exchange reaction and its application in solid-phase synthesis. Angew Chem Int Ed Engl 1998, 37:1701-1703. This work opens up, for the first time, one of the most important reactions in organic chemistry to the field of solid-phase synthesis.
20. Du XH, Armstrong RW: Sml2-mediated sequential radical cyclization/anionic capture of aryl iodides on solid support. Tetrahedron Lett 1998, 39:2281-2284.
21. Berteina S, De Mesmaeker A: Application of radical chemistry to solid support synthesis. Tetrahedron Lett 1998, 39:5759-5762.
22. Nicolaou KC, Vourloumis D, Li TH, Pastor J, Winssinger N, He Y, Ninkovic S, Sarabia F, Vallberg H, Roschangar F et al.: Designed epothilones: Combinatorial synthesis, tubulin assembly properties, and cytotoxic action against taxol-resistant tumor cells. Angew Chem Int Ed Engl 1997, 36:2097-2103.
23. Phoon CW, Abell C: Solid phase aldol and conjugate addition reactions using Evans' oxazolidinone chiral auxiliary. Tetrahedron Lett 1998, 39:2655-2658.
24. Winkler JD, McCoull W: Diels-Alder reaction on solid supports using polymer-bound oxazolidinones. Tetrahedron Lett 1998, 39:4935-4936.
25. Lee CE, Kick EK, Ellman JA: General solid-phase synthesis approach to prepare mechanism-based aspartyl protease inhibitor libraries. Identification of potent cathepsin D inhibitors. J Am Chem Soc 1998, 120:9735-9747. This is an example of the construction and screening of large libraries of stereochemically defined compounds.
26. Reggelin M, Brenig V, Welcker R: Towards polyketide libraries - II: Synthesis of chiral aracemic di- and triketides on a solid support. Tetrahedron Lett 1998, 39:4801-4804. This paper describes the optimisation of a previously reported strategy that allows the assembly of complex, stereochemically pure structures in an iterative fashion.
27. Gennari C, Ceccarelli S, Piarulli U, Aboutayab K, Donghi M, Paterson I: Stereocontrolled synthesis of polyketide libraries: Boron-mediated aldol reactions with aldehydes on solid support. Tetrahedron 1998, 54:14999-15016.
28. Wunberg T, Kallus C, Opatz T, Henke S, Schmidt W, Kunz H: Carbohydrates as multifunctional chiral scaffolds in combinatorial synthesis. Angew Chem Int Ed Engl 1998, 37:2503-2505.
29. Gray NS, Wodicka L, Thunnissen A, Norman TC, Kwon Sj, Espinoza FH, Morgan DO, Barnes G, LeClerc S, Meijer L et al.: Exploiting chemical libraries, structure, and genomics in the search for kinase inhibitors. Science 1998, 281:533-538. The discovery of new kinase inhibitors from a number of libraries, varying in their point of attachment to resin, is described.
30. Tan DS, Foley MA, Shair MD, Schreiber SL: Stereoselective synthesis of over two million compounds having structural features both reminiscent of natural products and compatible with miniaturized cell-based assays. J Am Chem Soc 1998, 120:8565-8566. Using very simple chemistry, the authors were able to generate vast compound libraries of relatively complex structure in a highly selective manner, without requiring protecting groups.
31. Xiao XY, Parandoosh Z, Nova MP: Design and synthesis of a taxoid library using radiofrequency encoded combinatorial chemistry. J Org Chem 1997, 62:6029-6033.
32. Nicolaou KC, Winssinger N, Vourloumis D, Ohshima T, Kim S, Pfefferkorn J, Xu JY, Li T: Solid and solution phase synthesis and biological evaluation of combinatorial sarcodictyin libraries. J Am Chem Soc 1998, 120:10814-10826.
33. Boger DL, Ducray P, Chai WY, Jiang WQ, Goldberg J: Higher order iminodiacetic acid libraries for probing protein-protein interactions. Bioorg Med Chem Lett 1998, 8:2339-2344.
34. Gravert DJ, Janda KD: Synthesis on soluble polymers: New reactions and the construction of small molecules. Curr Opin Chem Biol 1997, 1:107-113.
35. Studer A, Hadida S, Ferritto R, Kim SY, Jeger P, Wipf P, Curran DP: Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis. Science 1997, 275:823-826.
36. Hay AM, HobbsDewitt S, MacDonald AA, Ramage R: Use of tetrabenzo[a,c,g,i]fluorene as an anchor group for the solid/solution phase synthesis of Ciprofloxacin (R). Tetrahedron Lett 1998, 39:8721-8724. This describes an ingenious strategy, which combines conventional solution-phase chemistry with a facile 'pseudo-solid phase' purification procedure amenable to library synthesis.
37. Starkey GW, Parlow JJ, Flynn DL: Chemically-tagged Mitsunobu reagents for use in solution-phase chemical library synthesis. Bioorg Med Chem Lett 1998, 8:2385-2390. Modified chemical reagents that are easily removed post-reaction by solid-liquid extraction were designed to carry out the Mitsunobu reaction. This is a very clean procedure which deserves to be extended to a range of transformations.
38. Ley SV, Bolli MH, Hinzen B, Gervois AG, Hall BJ: Use of polymer supported reagents for clean multi-step organic synthesis: Preparation of amines and amine derivatives from alcohols for use in compound library generation. J Chem Soc Perkin Trans 1 1998:2239-2241.