Developments in solution-phase combinatorial chemistry

Current Opinion in Drug Discovery and Development

Volumn 2, Issue 4, 1999, Pages 377-384

  Suto, Mark J ^a  

^a Formerly CombiChem Inc   (United States)

Author keywords

Polymer supported chemistry; Purification; Scavenging techniques; Solution phase chemistry

Indexed keywords

POLYMER;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032804806     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Flynn DL, Devraj RV, Waing N, Partow JJ, Weidner JJ, Yang S. Polymer-assisted solution phase (PASP) chemical library synthesis. Med Chem Res (1998) 8:219-243.
2. Flynn DL, Devraj RV, Partow JJ. Recent advances in polymerassisted solution-phase chemical library synthesis and purification. Curr Opin Drug Disc Dev (1998) 1:41 -50.
3. •• A comprehensive review of new developments in this entire area.
4. Hulme C, Morrissette MM, Volz FA, Bums CJ. The solution phase synthesis of diketopiperazines via the Ugi reaction: Novel applications of Armstrong's convertible isonitrile. Tetrahedron Lett (1998) 39:1113-1116.
5. Song WK, Bauer SM, Armstrong RW. Multicomponent solution phase synthesis of dehydroamino acid derivatives based on the Passerini reaction. Tetrahedron Lett (1998) 39:7031-7034.
6. Fokas D, Ryan WJ, Casebier DS, Coffen DL. Solution phase synthesis of a spiro[pyrro!idine-2,3'-oxindole] library via a three component 1,3-dipolar cycloaddition reaction. Tetrahedron Lett (1998) 39:2235-2238.
7. Boger DL, Chai W, Jin Q. Multistep convergent solutionphase combinatorial synthesis and deletion synthesis deconvolution. JAm Chem Soc (1998) 120:7220-7225.
8. Bhat AS, Whetstone JL, Brueggemeier RW. Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries. Tetrahedron Lett (1999) 40:2469-2472.
9. Pitiik J, Townsend CA. Solution-phase synthesis of a combinatorial monocyclic -lactam library: Potential protease inhibitors. Bioorg Med Chem Lett (1997) 38:3129-3134.
10. Blackburn C, Guan B, Fleming P, Shiosaki K, Tsai S. Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation. Tetrahedron Lett (1998)39:3635-3638.
11. Panunzio M, Villa M, Missio A, Rossi T, Seneci P. Solution phase library of perhydrooxazin-4-ones. Tetrahedron Lett (1998)39:6585-6588.
12. Boger DL, Goldberg J, Andersson C-M. Solution phase combinatorial synthesis of biaryl libraries employing heterogeneous conditions for catalysis and isolation with size exclusion chromatography for purification. J Org Chem (1999) 64:2422-2427.
13. Florin! MT, Abell C. Solution-phase synthesis of 2,6,9-trisubstituted purines. Tetrahedron Lett (1998) 39:18271830.
14. Raju B, Kassir JM, Kogan TP. Solution-phase combinatorial synthesis of ureas using nitrophenylcarbamates. Bioorg Med Chem Lett (1998) 8:3043-3048.
15. • 7776 paper illustrates the use of several different types of scavengers.
16. Siegel M, Shuker A, Droste C, Hahn P, üesudason C, McDonald J, Matthews D, Rito C. Thorpe A: The use of highthroughput synthesis and purification In the preparation of a directed library of adrenergic agents. Mol Diversity (1998) 3:113-116.
17. Kulkami B, Ganesan A. Solution-phase combinatorial synthesis of 4-hydroxyquinolin-2(1 H)-ones. J Chem Soc Chem Commun (1998):785-786.
18. Maltais R, Poirer D. A solution-phase combinatorial parallel synthesis of 3-amido-3a-hydroxy-5ct-androstane-17-ones. Tetrahedron Z.ett(1998) 39:4151-4154.
19. Deegan T, Nitz T, Cebzanov D. Pufko D, Porco J: Parallel synthesis of 1,2,4-oxadiazoles using GDI activation. Bioorg Med Chem Lett (1999) 9:209-212.
20. Barrett A, Smith M, Zecri F. Impurity annihilation; a strategy for solution phase combinatorial chemistry with minimal purification. Chem Comm (1998) 4:2317-2318.
21. •• An interesting approach for the removal of excess reagents that provides an inexpensive method of doing so.
22. Nikam SS, Komberg BE, Ault-Justus SE, Rafferty MF. Novel quenchers for solution phase parallel synthesis. Tetrahedron /_ett(1998) 39:1121-1124.
23. Starkey GW, Partow JJ, Flynn DL. Chemically tagged Mitsunobu reagents for use in solution-phase chemical library synthesis. Bioorg Med Chem Lett (1998) 39:23852390.
24. • The use of masked reagents that can be chemically modified and then easily removed is demonstrated. This technique should be applicable to many common reagents.
25. Buckman BO, Monissey MM, Mohan R. Solution-phase parallel synthesis of benzoxazines using polymersupported carbodiimide. Tetrahedron Lett (1998) 39:14871488.
26. Ley SV. Bolli MH, Hinzen B, Gervois A-G, 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):2239-2242.
27. •• An excellent example of multi-step reactions (oxidation, reduction, acylation) using polymer-supported reagents.
28. Wei X, Mohan R, Morrissey MM. Polymer supported bases in solution-phase synthesis. 2. A convenient method for Nalkylation reactions of weakly acidic heterocycles. Bioorg Med Chem Lett (1998) 39:1089-1092.