Towards the synthesis of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors

Tetrahedron Letters

Volumn 51, Issue 48, 2010, Pages 6325-6328

  Olomola, Temitope O ^a   Klein, Rosalyn ^a   Lobb, Kevin A ^a   Sayed, Yasien ^b   Kaye, Perry T ^a  

^a RHODES UNIVERSITY   (South Africa)

^b UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; COPPER; COUMARIN DERIVATIVE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PHENPROCOUMON; PROTEINASE; PROTEINASE INHIBITOR; RITONAVIR; SALICYLALDEHYDE; VIRUS ENZYME; ZIDOVUDINE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; CYCLIZATION; CYCLOADDITION; DRUG STRUCTURE; EVALUATION; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; SYNTHESIS;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 78049430698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.121     Document Type: Article

References (33)

1. A.D. Frankel, and J.A.T. Young Annu. Rev. Biochem. 67 1998 1 25
2. R.T. Davey Jr., R.L. Dewar, G.F. Reed, M.B. Vasudevachari, M.A. Polis, J.A. Kovacs, J. Falloon, R.E. Walker, H. Masur, S.E. Haneiwich, D.G. O'Neill, M.R. Decker, J.A. Metcalf, M.A. Deloria, O.L. Laskin, N. Salzmant, and H.C. Lane Proc. Natl. Acad. Sci. U.S.A. 90 1993 5608 5612
3. R. Ragno, S. Frasca, F. Manetti, A. Brizzi, and S. Massa J. Med. Chem. 48 2005 200 212
4. I. Kostova, S. Raleva, P. Genova, and R. Argirova Bioinorg. Chem. Appl. 68274 2006 1 9
5. P.T. Kaye, M.A. Musa, A.T. Nchinda, and X.W. Nocanda Synth. Commun. 34 2004 2575 2589
6. C. Spino, M. Dodier, and S. Sotheeswaran Bioorg. Med. Chem. Lett. 8 1998 3475 3478
7. A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, and H. Ohigashi Bioorg. Med. Chem. Lett. 10 2000 59 62
8. Y. Xia, Z.-Y. Yang, P. Xia, T. Hackl, E. Hamel, A. Mauger, J.-H. Wu, and K.-H. Lee J. Med. Chem. 44 2001 3932 3936
9. M. Itoigawa, C. Ito, H.T.-W. Tan, M. Kuchide, H. Tokuda, H. Nishino, and H. Furukawa Cancer Lett. 169 2001 15 19
10. T. Yamaguchi, T. Fukuda, F. Ishibashi, and M. Iwao Tetrahedron Lett. 47 2006 3755 3757
11. Y. Yamamoto, and M. Kurazono Bioorg. Med. Chem. Lett. 17 2007 1626 1628
12. T.J. Rashamuse, M.A. Musa, R. Klein, and P.T. Kaye J. Chem. Res. 5 2009 302 305
13. A.S. Bourinbaiar, X. Tan, and R. Nagorny AID 7 1993 129 130
14. P.J. Tummino, D. Ferguson, L. Hupe, and D. Hupe Biochem. Biophys. Res. Commun. 200 1994 1658 1664
15. P.J. Tummino, D. Ferguson, and D. Hupe Biochem. Biophys. Res. Commun. 201 1994 290 294
16. J.V.N. Vara Prasad, K.S. Para, E.A. Lunney, D.F. Ortwine, J.B. Dunbar Jr., D. Ferguson, P.J. Tummino, D. Hupe, B.D. Tait, J.M. Domagala, C. Humblet, T.N. Bhat, B. Liu, D.M.A. Guerin, E.T. Baldwin, J.W. Erickson, and T.K. Sawyer J. Am. Chem. Soc. 116 1994 6989 6990
17. E.A. Lunney, S.E. Hagen, J.M. Domagala, C. Humblet, J. Kosinski, B.D. Tait, J.S. Warmus, M. Wilson, D. Ferguson, D. Hupe, P.J. Tummino, E.T. Baldwin, T.N. Bhat, B. Liu, and J.W. Erickson J. Med. Chem. 37 1994 2664 2677
18. P.T. Kaye, M.A. Musa, and X.W. Nocanda Synthesis 2003 531 534
19. P.T. Kaye, and M.A. Musa Synth. Commun. 34 2004 3409 3417
20. A. Brik, J. Alexandratos, Y.-C. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, D.S. Goodsell, and C.-H. Wong ChemBioChem 6 2005 1167 1169
21. D.J. Kempf, K.C. Marsh, J.F. Denissen, E. Mcdonald, S. Vasavanonda, C.A. Flentge, B.E. Green, L. Fino, C.H. Parks, X.-P. Kong, N.E. Wideburg, A. Saldivar, L. Ruiz, W.M. Kati, H.L. Sham, T. Robins, K.D. Stewart, A. Hsu, J.J. Plattner, J.M. Leonard, and D.W. Norbeck Proc. Natl. Acad. Sci. U.S.A. 92 1995 2484 2488
22. A. Wlodawer, and J. Vondrasek Annu. Rev. Biophys. Biomol. Struct. 27 1998 249 284
23. J. Ren, C. Nichols, L.E. Bird, T. Fujiwara, H. Sugimoto, D.I. Stuart, and D.K. Stammers J. Biol. Chem. 275 2000 14316 14320
24. J. Lindberg, S. Sigurdsson, S. Lowgren, H.O. Andersson, C. Sahlberg, R. Noreen, K. Fridborg, H. Zhang, and T. Unge Eur. J. Biochem. 269 2002 1670 1677
25. P.A. Furman, J.A. Fyfe, M.H. St. Clair, K. Weinhold, J.L. Rideout, G.A. Freeman, S.N. Lehrman, D.P. Bolognesi, S. Broder, H. Mitsuya, and D.W. Barry Proc. Natl. Acad. Sci. U.S.A. 83 1986 8333 8337
26. B. Schneider, R. Biondi, R. Sarfati, F. Agou, C. Guerreiro, D. Deville-Bonne, and M. Veron Mol. Pharmacol. 57 2000 948 953
27. E. De Clercq Int. J. Antimicrob. Agents 33 2009 307 320
28. 2O (50 mL) and brine (30 mL).
29. M. Mayer, and B. Meyer Angew Chem., Int. Ed. 38 1999 1784 1788
30. A. Velazquez-Campoy, M.J. Todd, S. Vega, and E. Freire Proc. Natl. Acad. Sci. U.S.A. 98 2001 6062 6067
31. Discovery Visual Studio, Release 2.0, San Diego, Accelrys Software Inc., 2007.
32. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639 1662
33. J. Gasteiger, and M. Marsili Tetrahedron 36 1980 3219 3228