Synthesis and biological evaluation of novel 5(H)-phenanthridin-6-ones, 5(H)-phenanthridin-6-one diketo acid, and polycyclic aromatic diketo acid analogs as new HIV-1 integrase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 3, 2007, Pages 1212-1228

  Patil, Shivaputra ^a   Kamath, Shantaram ^a   Sanchez, Tino ^b   Neamati, Nouri ^b   Schinazi, Raymond F ^c   Buolamwini, John K ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

HIV integrase inhibitors; Inhibition of HIV replication; Peripheral blood mononuclear cells; Phenanthridinone diketo acid; Phenanthridinones; Polycyclic aromatic diketo acids; Selectivity

Indexed keywords

1 [5 (4 FLUOROBENZYL) 2 FURYL] 3 (1,2,4 TRIAZOL 3 YL) 1,3 PROPANEDIONE; 1,3 DIKETONE; 2,4 DIOXO 4 (6 OXO 5,6 DIHYDROPHENANTHRIDIN 3 YL)BUTYRIC ACID; 2,4 DIOXO 4 PYREN 1 YLBUTYRIC ACID; 4 ANTHRACEN 2 YL 2,4 DIOXOBUTYRIC ACID; 4 ANTHRACEN 9 YL 2,4 DIOXOBUTYRIC ACID; INTEGRASE INHIBITOR; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHELATION; CONTROLLED STUDY; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; LIPOPHILICITY; MOLECULAR MODEL; PERIPHERAL BLOOD MONONUCLEAR CELL; SIMULATION; SUBSTITUTION REACTION; VIRUS REPLICATION;

ANIMALS; BUTYRIC ACIDS; CELL PROLIFERATION; CELLS, CULTURED; CERCOPITHECUS AETHIOPS; CRYSTALLOGRAPHY, X-RAY; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; KETO ACIDS; LEUKEMIA, LYMPHOID; LEUKOCYTES, MONONUCLEAR; MAGNESIUM; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENANTHRENES; PHENANTHRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33845934513     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.11.026     Document Type: Article

References (42)

1. UNAIDS 2006 Report on the Global AIDS Epidemic.
2. Coffin J.C., Hughes S.H., and Vermus H.E. Retroviruses (1999), Cold Spring Harbor Laboratory Press, Plainview, NY
3. Palella Jr. F.J., Delaney K.M., Moorman A.C., Loveless M.O., Fuhrer J., Satten G.A., Aschman D.J., and Holmberg S.D. N. Eng. J. Med. 338 (1998) 853-860
4. Bushman F., Landau N.R., and Emini E.A. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 11041-11042
5. De Clercq E. J. Med. Chem. 38 (1995) 2491-2517
6. Zhang L., Ramratnam B., Tenner-Racz K., He Y., Vesanen M., Lewin S., Talal A., Racz P., Perelson A.S., Korber B.T., Markowitz M., and Ho D.D. N. Eng. J. Med. 340 (1999) 1605-1613
7. Furtado M.R., Callaway D.S., Phair J.P., Kunstman K.J., Stanton J.L., Macken C.A., Perelson A.S., and Wolinsky S.M. N. Eng. J. Med. 340 (1999) 1614-1622
8. Brown P.O. Curr. Top. Microbiol. Immunol. 157 (1990) 19-48
9. Goff S.P. Annu. Rev. Genet. 26 (1992) 527-544
10. Katz R.A., and Skalka A.M. Annu. Rev. Biochem. 63 (1994) 133-173
11. Farnet C.M., Wang B., Lipford J.R., and Bushman F.D. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 9742-9747
12. Bushman F.D., and Craigie R. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 1339-1343
13. Brown P.O. Integration (1999), Cold Spring Harbor Press, Cold Spring Harbor
14. Asante-Appiah E., and Skalka A.M. Adv. Virus Res. 52 (1999) 351-369
15. Neamati N., Sunder S., and Pommier Y. DDT 2 (1997) 487
16. Neamati N. Expert. Opin. Investig. Drugs 10 (2001) 281
17. Fesen M.R., Pommier Y., Leteurtre F., Hiroguchi S., Yung J., and Kohn K.W. Biochem. Pharmacol. 48 (1994) 595
18. Marchand C., Neamati N., and Pommier Y. Methods Enzymol. 340 (2001) 624-633
19. Dayam R., and Neamati N. Curr. Pharm. Des. 9 (2003) 1789-1802
20. Neamati N. Expert Opin. Ther. Patent 12 (2002) 709-724
21. Dayam R., Deng J., and Neamati N. Med. Res. Rev. 26 (2006) 271-309
22. O'Neal, R. BETA 2006, 18, 13.
23. Rigby J.H., and Laurent S. J. Org. Chem. 63 (1998) 6742-6744
24. Ames D.E., and Opalko A. Tetrahedron 40 (1984) 1919-1925
25. DeRuiter J., Swearingen B.E., Wandekar V., and Mayfield C.A. J. Med. Chem. 32 (1989) 1033-1038
26. Ogata M., Matsumoto H., Shimizu S., Kida S., Wada T., Shiro M., and Sato K. J. Med. Chem. 29 (1986) 417-423
27. Pan H.L., and Fletcher T.L. J. Heterocycl. Chem. 7 (1970) 597
28. Aalten H.L., Koten G., Grove, David M., Kuilman T., and Piekstra O.G. Tetrahedron 45 (1989) 5565-5578
29. Couture C., and Paine A.J. Can. J. Chem. 63 (1985) 111-120
30. Li J.H., Serdyuk L., Ferraris D.V., Xiao G., Tays K.L., Kletzly P.W., Li W., Lautar S., Zhang J., and Kalish V.J. Bioorg. Med. Chem. Lett. 11 (2001) 1687
31. Hazuda D.J., Felock P., Witmer M., Wolfe A., Stillmock K., Grobler J.A., Espeseth A., Garbryelski L., Schleif W., Blau C., and Miller M.D. Science 287 (2000) 646
32. Fikkert V., Van Maele B., Vercammen J., Hantson A., Van Remoortel B., Michiels M., Gurnari C., Pannecouque C., De Maeyer M., Engelborghs Y., De Clercq E., Debyser Z., and Witvrouw M. J. Virol. 77 (2003) 11459-11470
33. Pannecouque C., Pluymers W., Van Maele B., Tetz V., Cherepanov P., De Clercq E., Witvrouw M., and Debyser Z. Curr. Biol. 12 (2002) 1169-1177
34. Marchand C., Johnson A.A., Karki R.G., Pais G.C., Zhang X., Cowansage K., Patel T.A., Nicklaus M.C., Burke Jr. T.R., and Pommier Y. Mol. Pharmacol. 63 (2003) 600-609
35. Jones G., Willet P., Glen R.C., Leach A.R., and Taylor R. J. Mol. Biol. 267 (1997) 727
36. Goldgur Y., Dyda F., Hickman A.B., Jenkins T.M., Cragie R., and Davies D.R. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 9150-9154
37. Marchand C., Johnson A.A., Karki R.G., Pais G.C., Zhang X., Cowansage K., Patel T.A., Nicklaus M.C., Burke Jr. T.R., and Pommier Y. Mol. Pharmacol. 64 (2003) 600-609
38. Stuyver L.J., Lostia S., Adams M., Mathew J.S., Pai B.S., Grier J., Tharnish P.M., Choi Y., Chong Y., Choo H., Chu C.K., Otto M.J., and Schinazi R.F. Antimicrob. Agents Chemother. 46 (2002) 3854-3860
39. Schinazi R.F., Sommadossi J.P., Saalmann V., Cannon D.L., Xie M.Y., Hart G.C., Smith G.A., and Hahn E.F. Antimicrob. Agents Chemother. 34 (1990) 1061-1067
40. Sommadossi J.P., Carlisle R., Schinazi R.F., and Zhou Z. Antimicrob. Agents Chemother. 32 (1988) 997-1001
41. Schinazi R.F., Peters J., Williams C.C., Chance D., and Nahmias A.J. Antimicrob. Agents Chemother. 22 (1982) 499-507
42. Goldgur Y., Craigie R., Cohen G.H., Fujiwara T., Yoshinaga T., Sugimoto H., Endo T., Murai H., and Davies D.R. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 13040