HIV-1 replication inhibitors of the styrylquinoline class: Introduction of an additional carboxyl group at the C-5 position of the quinoline

Tetrahedron Letters

Volumn 46, Issue 13, 2005, Pages 2201-2205

  Zouhiri, Fatima ^a,b   Danet, Michèle ^a   Bénard, Christophe ^a   Normand Bayle, Marie ^a   Mouscadet, Jean François ^a   Leh, Hervé ^b   Marie Thomas, Claire ^b   Mbemba, Gladys ^a   D'Angelo, Jean ^a   Desmaële, Didier ^a  

^a CNRS   (France)

^b BioAlliance Pharma   (France)

Author keywords

Antivirals; Carbonylation; Enzyme inhibitors; Heck reactions; Quinolines

Indexed keywords

ACRYLIC ACID; CARBOXYL GROUP; INTEGRASE INHIBITOR; PALLADIUM; QUINALDINE DERIVATIVE; QUINOLINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CARBONYLATION; CATALYSIS; DRUG SYNTHESIS; HECK REACTION; HUMAN IMMUNODEFICIENCY VIRUS 1; VIRUS INHIBITION; VIRUS REPLICATION;

EID: 20044376086     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.033     Document Type: Article

References (30)

1. E. De Clercq Med. Res. Rev. 22 2002 531 565
2. P.O. Brown Curr. Top. Microbiol. Immunol. 157 1990 19 48
3. A.S. Espeseth, P. Felock, A. Wolfe, M. Witmer, J. Grobler, N. Anthony, M. Egbertson, J.Y. Melamed, S. Young, T. Hamill, J.L. Cole, and D.J. Hazuda Proc. Natl. Acad. Sci. U.S.A. 97 2000 11244 11249
4. D.J. Hazuda, N.J. Anthony, R.P. Gomez, S.M. Jolly, J.S. Wai, L. Zhuang, T.E. Fisher, M. Embrey, J.P. Guare Jr., M.S. Egbertson, J.P. Vacca, J.R. Huff, P.J. Felock, M.V. Witmer, K.A. Stillmock, R. Danovich, J. Grobler, M.D. Miller, A.S. Espeseth, L. Jin, I.W. Chen, J.H. Lin, K. Kassahun, J.D. Ellis, B.K. Wong, W Xu, P.G. Pearson, W.A. Schlief, R Cortese, E. Emini, V. Summal, M.K. Holloway, and S.D. Young Proc. Natl. Acad. Sci. U.S.A. 101 2004 11233 11238
5. R. Costi, R. Di Santo, M. Artico, S. Massa, R. Ragno, R. Loddo, M. La Colla, E. Tramontano, P. La Colla, and A. Pani Bioorg. Med. Chem. 12 2004 199 215
6. T. Middleton, H.B. Lim, D. Montgomery, T. Rockway, H. Tang, X. Cheng, L. Lu, H. Mo, W.E. Kohlbrenner, A. Molla, and W.M. Kati Antiviral Res. 64 2004 35 45
7. K. Mekouar, J.-F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo J. Med. Chem. 41 1998 2846 2857
8. F. Zouhiri, J.-F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo J. Med. Chem. 43 2000 1533 1540
9. M. Ouali, C. Laboulais, H. Leh, D. Gill, D. Desmaële, K. Mekouar, F. Zouhiri, J. d'Angelo, C. Auclair, J.-F. Mouscadet, and M. Le Bret J. Med. Chem. 43 2000 1949 1957
10. F. Zouhiri, D. Desmaële, J. d'Angelo, M. Ourevitch, J.-F. Mouscadet, H. Leh, and M. Le Bret Tetrahedron Lett. 42 2001 8189 8192
11. J. Polanski, F. Zouhiri, L. Jeanson, D. Desmaële, J. d'Angelo, J.-F. Mouscadet, R. Gieleciak, J. Gasteiger, and M. Le Bret J. Med. Chem. 45 2002 4647 4654
12. C. Bénard, F. Zouhiri, M. Normand-Bayle, M. Danet, D. Desmaële, H. Leh, J.-F. Mouscadet, G. Mbemba, C.-M. Thomas, S. Bonnenfant, M. Le Bret, and J. d'Angelo Bioorg. Med. Chem. Lett. 14 2004 2473 2476
13. E. Deprez, S. Barbe, M. Kolaski, H. Leh, F. Zouhiri, C. Auclair, J.-C. Brochon, M. Le Bret, and J.-F. Mouscadet Mol. Pharmacol. 65 2004 85 98
14. S. Bonnenfant, M.-C. Thomas, C. Vita, F. Subra, E. Deprez, F. Zouhiri, D. Desmaële, J. d'Angelo, J.-F. Mouscadet, and H. Leh J. Virol. 78 2004 5728 5736
15. W.H. Meek, and C.H.J. Fuschman J. Chem. Eng. Data 14 1969 388 391
16. The halodecarboxylation of salicylic acids has been previously reported: E. Grovenstein Jr., and U.V. Henderson Jr. J. Am. Chem. Soc. 78 1956 569 578
17. 6, 100 MHz) δ 169.5 (C), 167.9 (C), 163.1 (C), 152.3 (C), 149.1 (C), 146.2 (C), 142.1 (CH), 139.0 (CH), 138.2 (CH), 134.3 (C), 128.8 (C), 127.9 (CH), 127.5 (C), 121.9 (CH), 121.4 (CH), 118.7 (CH), 118.3 (CH), 116.5 (CH), 115.8 (C), 114.9 (CH), 114.0 (C)
18. T. Kometani, D.S. Watt, and T. Ji Tetrahedron Lett. 26 1985 2043 2046 A better yield was obtained by adding quinaldine 11 to a preformed mixture of sodium iodide and chloramine-T
19. B.A. Anderson, E.C. Bell, F.O. Ginah, N.K. Harn, L.M. Pagh, and J.P. Wepsiec J. Org. Chem. 63 1998 8224 8228
20. H. Fiedler Arch. Pharm. Ber. 293 1960 609 621
21. K. Matsumura, and M. Ito J. Org. Chem. 25 1960 853 854
22. R.C. Gadwood, M.R. Rubino, S.C. Nagarajan, and S.T. Michel J. Org. Chem. 50 1985 3255 3260
23. F. Marsais, Ph. Pineau, F. Nivolliers, M. Mallet, A. Turck, A. Godard, and G. Queguiner J. Org. Chem. 57 1992 565 573
24. An improved yield was observed using methanol as co-solvent, but extensive trans-esterification occurred in such conditions
25. N.A. Bumagin, K.V. Nikitin, and I.P. Beletskaya J. Organomet. Chem. 358 1988 563 565
26. M.S. Yu, and N.H. Baine Tetrahedron Lett. 40 1999 3123 3124
27. 2O: C, 58.68; H, 4.02; N, 3.42. Found: C, 58.53; H, 4.21; N, 3.36
28. 19
29. D.C. Eustice, P.A. Feldman, A.M. Colberg-Poley, R.M. Buckery, and R.H. Neubauer BioTechniques 11 1991 739 740
30. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271 277