Diversity-oriented synthesis of a drug-like system displaying the distinctive N→C=O interaction

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6119-6126

  Waibel, Michael ^a   Hasserodt, Jens ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIVERSITY-ORIENTED SYNTHESIS; SIX-MEMBERED RINGS;

CHEMICAL REACTIONS; CHEMOTHERAPY; DRUG DELIVERY; DRUG DOSAGE; DRUG INTERACTIONS; UREA;

SYNTHESIS (CHEMICAL);

AMINO ACID; ENZYME; FUNCTIONAL GROUP; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; METHANOL; PEPTIDE; PROTEINASE INHIBITOR; UREA DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

ALDEHYDES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HIV PROTEASE; HIV-1; HYDRAZINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PIPERIDINES; PROLINE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THERMODYNAMICS; UREA;

EID: 50149117209     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800719j     Document Type: Article

References (45)

1. Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 383, 60-63.
2. Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97, 1281-1301.
3. Wolfenden, R. Bioorg. Med. Chem. 1999, 7, 647-652.
4. Abbenante, G.; Fairlie, D. P. Med. Chem. 2005, 7, 71-104.
5. De Clercq, E. Nat. Rev. Drug Discov. 2007, 6, 1001-1018.
6. Brik, A.; Wong, C. H. Org. Biomol. Chem. 2003, 7, 5-14.
7. Bursavich, M. G.; Rich, D. H. J. Med. Chem. 2002, 45, 541-558.
8. Ghosh, A. K.; Chapsal, B. D.; Weber, I. T.; Mitsuya, H. Acc. Chem. Res. 2008, 41, 78-86.
9. DeLucca, G. V.; EricksonViitanen, S.; Lam, P. Y. S. Drug Discovery Today 1997, 2, 6-18.
10. Hagen, S.; Prasad, J. V. N. V.; Tait, B. D. Adv. Med. Chem. 2000, 5, 159-195.
11. Thaisrivongs, S.; Strohbach, J. W. Biopolymers 1999, 51, 51-58.
12. Dunitz, J. D. Science 1994, 264, 670-670.
13. Dunn, B. M. Chem. Rev. 2002, 102, 4431-4458.
14. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615-2623.
15. Maly, D. J.; Huang, L.; Ellman, J. A. ChemBioChem 2002, 3, 16-37.
16. Reymond, J. L. Angew. Chem., Int. Ed. 2004, 43, 5577-5579.
17. McCrindle, R.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 61-62.
18. Becker, M. H.; Chua, P.; Downham, R.; Douglas, C. J.; Garg, N. K.; Hiebert, S.; Jaroch, S.; Matsuoka, R. T.; Middleton, J. A.; Ng, F. W.; Overman, L. E. J. Am. Chem. Soc. 2007, 129, 11987-12002.
19. Gautier, A.; Pitrat, D.; Hasserodt, J. Bioorg. Med. Chem. 2006, 14, 3835-3847.
20. Okimoto, N.; Tsukui, T.; Hata, M.; Hoshino, T.; Tsuda, M. J. Am. Chem. Soc. 1999, 121, 7349-7354.
21. Piana, S.; Bucher, D.; Carloni, P.; Rothlisberger, U. J. Phys. Chem. B 2004, 108, 11139-11149.
22. Kermack, W. O.; Robinson, R. J. Chem. Soc. 1922, 121, 427-441.
23. Leonard, N. J. Rec. Chem. Prog. 1956, 17, 243-257.
24. Rademacher, P. Chem. Soc. Rev. 1995, 24, 143-150.
25. Leonard, N. J.; Morrow, D. F.; Rogers, M. T. J. Am. Chem. Soc. 1957, 79, 5476-5479.
26. Leonard, N. J.; Oki, M. J. Am. Chem. Soc. 1955, 77, 6239-6240.
27. (a) Davies, J. E.; Kirby, A. J.; Komarov, I. V. Helv. Chim. Acta 2003, 86, 1222-1233.
28. (b) Kirby, A. J.; Komarov, I. V.; Bilenko, V. A.; Davies, J. E.; Rawson, J. M. Chem. Commun. 2002, 2106-2107.
29. (c) Carroll, J. D.; Jones, P. R.; Ball, R. G. J. Org. Chem. 1991, 56, 4208-4213.
30. (d) Pilme, J.; Berthoumieux, H.; Robert, V.; Fleurat-Lessard, P. Chem.-Eur. J. 2007, 13, 5388-5393.
31. (e) Bell, M. R.; Archer, S. J. Am. Chem. Soc. 1960, 82, 151-155.
32. Vidal, J.; Damestoy, S.; Guy, L.; Hannachi, J. C.; Aubry, A.; Collet, A. Chem.-Eur. J. 1997, 3, 1691-1709.
33. Smith, R. F.; Brophy, K. A.; Rodriguez, G.; Dennis, L. A.; Ryan, W. J. Synth. Commun. 1990, 20, 183-188.
34. Kurz, T.; Widyan, K. Tetrahedron Lett. 2004, 45, 7049-7051.
35. Grzyb, J. A.; Shen, M.; Yoshina-Ishii, C.; Chi, W.; Brown, R. S.; Batey, R. A. Tetrahedron 2005, 61, 7153-7175.
36. Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; DeLucca, G. V.; Eyermann, C. J.; Chang, C. H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L. Z.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Li, R. H.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L. Y.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; EricksonViitanen, S.; Hodge, C. N. J. Med. Chem. 1996, 39, 3514-3525.
37. Perdicchia, D.; Licandro, E.; Maiorana, S.; Baldoli, C.; Giannini, C. Tetrahedron 2003, 59, 7733-7742.
38. Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607.
39. Jung, M. E.; Andrus, W. A.; Ornstein, P. L. Tetrahedron Lett. 1977, 4175-4178.
40. Klosterman, H. J.; Lamoureux, G. L.; Parsons, J. L. Biochemistry 1967, 6, 170-177.
41. Vidal, J.; Hannachi, J. C.; Hourdin, G.; Mulatier, J. C.; Collet, A. Tetrahedron Lett. 1998, 39, 8845-8848.
42. Li, W. H.; Hanau, C. E.; d'Avignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155-8170.
43. Zhao, Y. M.; Raymond, M. K.; Tsai, H.; Roberts, J. D. J. Phys. Chem. 1993, 97, 2910-2913.
44. Drakenberg, T.; Dahlqvist, K.-I.; Forsen, S. J. Phys. Chem. 1972, 76, 2178-2183.
45. Scherer, G.; Kramer, M. L.; Schutkowski, M.; Reimer, U.; Fischer, G. J. Am. Chem. Soc. 1998, 120, 5568-5574.