Solution-phase synthesis of mixed amide libraries by simultaneous addition of functionalities (SPSAF) to a diketopiperazine tetracarboxylic acid scaffold monitored by GC analysis of isobutyl alcohol

European Journal of Organic Chemistry

Volumn , Issue 8, 2000, Pages 1669-1675

  Falorni, Massimo ^a   Giacomelli, Giampaolo ^a   Porcheddu, Andrea ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Amides; Combinatorial chemistry; Gas chromatography

Indexed keywords

ISOBUTANOL; OLIGOMER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034057752     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200004)2000:8<1669::AID-EJOC1669>3.0.CO;2-R     Document Type: Article

References (32)

1. R. E. Dolle, K. H. Kingsley Jr., J. Comb. Chem. 1999, 1, 235-282.
2. S. Borman, Chem. Eng. News 1999, 8, 33-48.
3. R. Dagani, Chem. Eng. News 1999, 8, 51-60.
4. L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600.
5. E. N. Jacobsen, M. B. Francis, Angew. Chem. Int. Ed. 1999, 38, 937-941.
6. R. Schlögl. Angew. Chem. Int. Ed. 1998, 37, 2333-2336.
7. S. Kobajashi, Chem. Soc. Rev. 1999, 28, 1-74.
8. M. J. Suto, L. M. Gayo-Fung, M. S. S Palanki, R. Sullivan, Tetrahedron 1998, 54, 4141-4150.
9. D. L. Boger, W. Chai, R. S. Ozer, C.-M. Andersson, Bioorg. Med. Chem. Lett. 1997, 7, 463-468.
10. D. L. Flynn, J. Z. Crich, R. V. Devraj, S. L. Hockerman, J. J. Parlow, M. S. South, S. Woodard, J. Am. Chem. Soc. 1997, 119, 4874-4881.
11. S. Cheng, D. D. Comer, J. P. Williams, P. L. Myers, D. L. Boger, J. Am. Chem. Soc. 1996, 118, 2567-2573.
12. S. W. Kaldor, M. G. Siegel, Curr. Opin. Chem. Biol. 1997, 1, 101-124.
13. K. E. Pryor, G. W. Shipps Jr., D. A. Skyler, J. Rebek Jr., Tetrahedron 1998, 54, 4107-4124.
14. J. J. Parlow, D. L. Flynn, Tetrahedron 1998, 54, 4013-4031.
15. A. K. Szardenings, D. Harris, S. Lam, L. Shi, D. Tien, Y. Wang, D. V. Patel, M. Navre, D. A. Campbell, J. Med. Chem. 1998, 47, 2194-2200.
16. M. W. Creswell, G. L. Bolton, J. C. Hodges, M. Meppen, Tetrahedron 1998, 54, 3983-3998.
17. K. E. Pryor, J. Rebek Jr., Org. Lett. 1999, 1, 39-42.
18. M. Falorni, G. Giacomelli, F. Nieddu, M. Taddei, Tetrahedron Lett. 1997, 38, 4663-4666.
19. C.-B. Cui, H. Kakeya, H. Osada, Tetrahedron 1996, 52, 12651-12660; J. Antibiot. 1996, 49, 534-538.
20. C.-B. Cui, H. Kakeya, H. Osada, Tetrahedron 1996, 52, 12651- 12660; J. Antibiot. 1996, 49, 534-538.
21. P. A. Charlton, R. W. Faint, F. Bent, J. Bryans, L. Chicarelli-Robinson, I. Mackie, S. Machin, P. Bevan, Thromb. Haemost. 1996, 75, 808-812.
22. Y. Funabashi, T. Horiguchi, S. Iinuma, S. Tanida, S. Harada, J. Antibiot. 1994, 47, 1202-1210.
23. J. H. Weng, A. Bado, C. Garbay, B. P. Roques, Reg. Pept. 1996, 65, 3-12.
24. V. S. Goodfellow, C. P. Laudeman, J. I. Gerrity, M. Burkard, E. Strobel, J. S. Zuzack, D. A. McLeod, Mol. Diver. 1996, 2, 1202-1212.
25. H. An, L. L. Cummins, R. H. Griffey, R. Bharadwaj, B. D. Haly, A. S. Fraser, L. Wilson-Lingardo, L. M. Risen, J. R. Wyatt, P. D. Cook. J. Am. Chem. Soc. 1997, 119, 3696-3708 and references therein.
26. R. H. Griffey, H. An, L. L. Cummins, H. J. Gaus, B. Haly, R. Herrmann, P. D. Cook, Tetrahedron 1998, 54, 4067-4076.
27. T. Carrel, E. A. Wintner, A. J. Sutherland, J. Rebek Jr., Y. M. Dunayevskiy, P. Vouros, Chem Biol. 1995, 2, 171-180.
28. C. L. Brummel, I. N. W. Lee, Y. Zhou, S. J. Benkovic, N. Winograd, Science 1994, 264, 386-389.
29. The four carboxylic groups of the core were named as the cardinal points: this notation is used throughout the paper.
30. E. Fischer, E. Koenigs, Chem. Ber. 1907, 40, 2048.
31. G. W. Anderson, J. Blodinger, R. W. Young, A. D. Welcher, J. Am. Chem. Soc. 1952, 74, 5304-5307.
32. M. Bodanszky, V. du Vigneaud, J. Am. Chem. Soc. 1959, 81, 2504-2510.