A novel strategy to assemble the β-diketo acid pharmacophore of HIV integrase inhibitors on purine nucleobase scaffolds

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8577-8579

  Uchil, Vinod ^a   Seo, Byung ^a   Nair, Vasu ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETO ACIDS; ENOLIC ETHER; PURINE NUCLEOBASE SCAFFOLDS;

ACYLATION; CATALYST ACTIVITY; ETHERS; HYDROLYSIS; NITROGEN COMPOUNDS; PALLADIUM COMPOUNDS;

ENZYME INHIBITION;

1 [5 (4 FLUOROBENZYL) 2 FURYL] 3 (1,2,4 TRIAZOL 3 YL) 1,3 PROPANEDIONE; 4 [1 (4 FLUOROBENZYL) 2 PYRROLYL] 2,4 DIOXOBUTYRIC ACID; BETA DIKETOACID; ESTER; INTEGRASE INHIBITOR; OXOACID; PALLADIUM; PURINE NUCLEOSIDE; PYRIMIDINE DERIVATIVE; PYRIMIDINE DIKETOACID; UNCLASSIFIED DRUG;

ACYLATION; ADDITION REACTION; ARTICLE; CLAISEN CONDENSATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; HUMAN IMMUNODEFICIENCY VIRUS; HYDROLYSIS; PHARMACOPHORE; REACTION ANALYSIS; STILLE REACTION; STRUCTURAL GENE;

HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HYDROLYSIS; KETO ACIDS; MOLECULAR STRUCTURE; PURINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35548969410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701336r     Document Type: Article

References (33)

1. Fauci, A. S. Science 1988, 239, 617.
2. Frankel, A. D.; Young, J. A. T. Annu. Rev. Biochem. 1998, 67, 1.
3. De Clercq, E. Nat. Rev. Drug Discovery 2002, 1, 13.
4. Johnson, S. C.; Gerber, J. G. In Advances in Internal Medicine; Schrier, R. W., Baxter, J. D., Dzau, V. J., Fauci, A. S., Eds.; Mosby: St. Louis, MO, 2000; Vol. 45, pp 1-40.
5. Nair, V.; St. Clair, M. H.; Reardon, J. E.; Krasny, H. C.; Hazen, R. J.; Paff, M. T.; Boone, L. R.; Tisdale, M.; Najera, I.; Domsife, R. E.; Averett, D. R.; Borroto-Esoda, K.; Yale, J. L.; Zimmerman, T. P.; Rideout, J. L. Antimicrob. Agents Chemother. 1995, 39, 1993.
6. De Clercq, E. J. Med. Chem. 2005, 48, 1297.
7. Pommier, Y.; Johnson, A. A.; Marchand, C. Nat. Rev. Drug Discovery 2005, 4, 236.
8. Nair, V. Frontiers Med. Chem. 2005, 2, 3.
9. Dayam, R.; Neamati, N. Curr. Pharm. Des. 2003, 9, 1789.
10. Nair, V.; Chi, G. Rev. Med. Virol. 2007, 17, 277.
11. Maurin, C.; Bailly, F.; Cotelle, P. Curr. Med. Chem. 2003, 10, 1795.
12. Neamati, N. Expert Opin. Ther. Pat. 2002, 12, 709.
13. Billich, A. Curr. Opin. Investig. Drugs (Thompson Sci.) 2003, 4, 206.
14. Hazuda, D. J.; Felock, P.; Witmer, M.; Wolfe, A.; Stillmock, K.; Grobler, J. A.; Espeseth, A.; Gabryelski, L; Schleif, W.; Blau, C.; Miller, M. D. Science 2000, 287, 646.
15. Selnick, H. G.; Hazuda, D. J.; Egbertson, M.; Guare, J. P.; Wai, J. S.; Young, S. D.; Clark, D. L.; Medina, J. C. PCT, WO 62513, 1999.
16. Nair, V.; Chi, G.; Ptak, R.; Neamati, N. J. Med. Chem. 2006, 49, 445.
17. Nair, V.; Uchil, V.; Neamati, N. Bioorg. Med. Chem. Lett. 2006, 16, 1920.
18. Williams, H. W. R.; Eicher, E.; Randell, W. C.; Rooney, C. S.; Cragoe, E. J., Jr.; Streeter, K. B.; Schwam, H.; Michelson, S. R.; Patchett, A. A.; Taub, D. J. Med. Chem. 1983, 26, 1196.
19. Pais, G. C. G.; Zhang, X.; Marchand, C.; Neamati, N.; Cowansage, K.; Svarovskaia, E. S.; Pathak, V. K.; Tang, Y.; Nicklaus, M.; Pommier, Y.; Burke, T. R. J. Med. Chem. 2002, 45, 3184.
20. Yuan, J.; Gulianello, M.; De Lombaert, S.; Brodbeck, R.; Kieltyka, A.; Hodgetts, K. J. Bioorg. Med. Chem. Lett. 2002, 12, 2133.
21. Jiang, X.-H.; Song, L.-D.; Long, Y.-Q. J. Org. Chem. 2003, 68, 7555.
22. Nair, V.; Young, D. A.; De Silvia, R. J. Org. Chem. 1987, 52, 1344.
23. Nair, V.; Turner, G. A.; Buenger, G. S.; Chamberlain, S. D. J. Org. Chem. 1988, 53, 3051.
24. Gundersen, L.-L.; Bakkestuen, A. K.; Aasen, J. A.; Øverås, H.; Rise, F. Tetrahedron 1994, 50, 9743.
25. Tietze, L-F.; Meier, H.; Foss, E. Synthesis 1988, 274.
26. March, J. Advanced Organic Chemistry, Reactions, Mechanisms and Structures, 4th ed.; John Wiley & Sons: New York, 1999; p 599.
27. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
28. March, J. Advanced Organic Chemistry, Reactions, Mechanisms and Structures, 4th ed.; John Wiley & Sons: New York, 1999; p 375.
29. Fadel, A.; Yefsah, R.; Salaun, J. Synthesis 1987, 37.
30. Ikemoto, N.; Kim, O. K.; Lo, L-C.; Satyanarayana, V.; Chang, M.; Nakanishi, K. Tetrahedron Lett. 1992, 33, 4295.
31. Kim, K. S.; Song, Y. H.; Lee, B. H.; Hahn, C. S. J. Org. Chem. 1986, 51, 404.
32. Sen, S. E.; Roach, S. L.; Boggs, J. K.; Ewing, G. J.; Magrath, J. J. Org. Chem. 1997, 62, 6684.
33. Summa, V.; Petrocchi, A.; Pace, P.; Matassa, V. G.; De Francesco, R.; Altamura, S.; Tomei, L.; Koch, U.; Neuner, P. J. Med. Chem. 2004, 47, 14.