Synthesis of compound libraries based on 3,4-diaminocyclopentanol scaffolds

Journal of Combinatorial Chemistry

Volumn 2, Issue 4, 2000, Pages 297-300

  Guan, Yousheng ^a   Green, Mark A ^a   Bergstrom, Donald E ^a,b  

^a PURDUE UNIVERSITY   (United States)

^b WALTHER CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANOL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINES; CYCLOPENTANES; DRUG DESIGN; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0040431570     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc990053g     Document Type: Article

References (21)

1. (a) Ellman, J. A. Synthesis, and Evaluation of Small-Molecule Libraries. Acc. Chem. Res. 1996, 29, 132-143.
2. (b) Gordon, E. M.: Barret, E. W.; Dower, W. J.; Fodor, S. P.; 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. (c) DeWitt, S. H.; Kelly, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M.; Pavia, M. R. Diversomers: An Approach to Nonpeptide, Nonoligomeric Chemical Diversity. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-13.
4. (d) Thompson, L. A.; Ellman, J. A.; Synthesis and Applications of Small Molecule Libraries. Chem. Rev. 1996, 96, 555-600.
5. (e) Balkenhonh, F.; Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Combinatorial Synthesis of Small Organic Molecules. Angew: Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
6. (f) Wong, C.-H.; Hendrix, M.; Manning, D. D.; Rosenbohm, C.; Greenberg, W. A. A Library Approach to the Discovery of Small Molecules That Recognize RNA: Use of a 1,3-Hydroxyamine Motiff as Core. J. Am. Chem. Soc. 1998, 120, 8319-8327.
7. (g) Osborne, S. E.; Ellington, A. D. Nucleic Acid Selection and the Challenge of Combinatorial Chemistry. Chem. Rev. 1997, 97, 349-370.
8. (a) Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengler, P. A.: Furst, G.; Smith, A. B., III; Strader, C. D.; Cascieri, M. A.; Candelore, M. R.; Donaldson, C.; Vale, W.; Maechler, L. Nonpeptidal Peptidomimetics with a β-D-Glucose Scaffolding. A Partial Somatostatin Agonist Bearing a Close Structural Relationship to a Potent, Selective Substance P Antagonist. J. Am. Chem. Soc. 1992, 114, 9217-9218.
9. (b) Hirschmann, R.; Sprengler, P. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B., III. The First Design and Synthesis of a Steroidal Peptidomimetic. The Potential Value of Peptidomimetics in Elucidating the Bioactive Conformation of Peptide Ligand. J. Am. Chem. Soc. 1992, 114, 9699-9701.
10. (c) Hirschmann, R.; Hynes, J., Jr.; Cichy-Knight, M. A.; van Rijn, R. D.; Sprengler, P. A.; Spoors, P. G.; Shakespeare, W. C.; Pietranico-Cole, S.; Barbosa, J.; Liu, J.; Yao, W.; Rohrer, S.; Smith, A. B., III. Modulation of Receptor and Receptor Subtype Affinities Using Diastereomeric and Enantiomeric Monosaccharide Scaffolds as a Means to Structural and Biological Diversity. A New Route to Ether Synthesis. J. Med. Chem. 1998, 41, 1382-1391.
11. (d) Holmes, C. P.; Chinn, J. P.; Look, G. C.; Gordon, E. R.; Gallop, M. A. Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids. J. Org. Chem. 1995, 60, 7328-7333.
12. (e) Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Kemp's Triacid Scaffolding for Synthesis of Combinatorial Nonpeptide Uncoded Libraries. Tetrahedron Lett. 1995, 36, 6623-6626.
13. (f) Feng, Y.; Melacini, G.; Taulane, J. P.; Goodman, M. Acetyl-Terminated and Template-Assemled Collagen-Based Polypeptides Composed of Gly-Pro-Hyp Sequences. 2. Synthesis and Comformational Analysis by Circular Dichroism, Ultraviolet Absorbance, and Optical Rotation. J. Am. Chem. Soc. 1996, 118, 10351-10358.
14. Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. 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.
15. Kirk, E. K.; Rose, D. C.; Skillman, A. G.; Liu, G.; Ewing, T. J.; Sun, Y.; Kuntz, I. D.; Ellman, J. A. Structural-based Design and Combinatorial Chemistry Yield Low Nanomolar Inhibitors of Cathepsin D. Chem. Biol. 1997, 4, 297-307.
16. Petek, M.; Drake, B.; Lebl, M. All-cis Cyclopentane Scaffolding for Combinatorial Solid-Phase Synthesis of Small Non-Peptide Compounds. Tetrahedron Lett. 1994, 35, 9169-9172.
17. Carell, T.; Winter, E. A.; Bashir-Hashemi, A.; Rebek, J., Jr. A Solution-Phase Screening Procedure for the Isolation of Active Compounds from a Library of Molecules. Angew. Chem., Int. Ed. Engl. 1994, 33, 2059-2061.
18. Boger, D. L.; Tarby, C. M.; Myers, P. L.; Caporale, L. H. Generalized Dipeptidomimetic Template: Solution Phase Parallel Synthesis of Combinatorial Libraries. J. Am. Chem. Soc. 1996, 118, 2109-2110.
19. Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Combinatorial Libraries Based on a Novel and Readily Accessible "Centroid" Scaffold. Tetrahedron Lett. 1998, 39, 5317-5320.
20. Davis, P. W.; Osgood, S. A.; Hebert, N.; Sprakle, K. G.; Swayze, E. E.; Solid-Phase Synthesis of a Library of Functionalized Aminodiol Scaffolds. Biotechnol. Bioeng. (Comb. Chem.) 1998/1999, 61, 143-154.
21. Guan, Y.; Green, M. A.; Bergstrom, D. E. Stereocontrolled Synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4-diaminocyclopentanols. Synlett 1999, 426-428.