Linker-modified quinoline derivatives targeting HIV-1 integrase: Synthesis and biological activity

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 10, 2004, Pages 2473-2476

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

^a UNIVERSITÉ PARIS SUD   (France)

^b BioAlliance Pharma   (France)

^c Ecole Normale Superieure de Cachan   (France)

Author keywords

Amides; Antivirals; Enzyme inhibitors; Quinolines; Ureas

Indexed keywords

AMIDE; ENZYME INHIBITOR; HYDRAZIDE; INTEGRASE; QUINOLINE DERIVATIVE; UREA; VIRUS ENZYME;

ARTICLE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; STRUCTURE ACTIVITY RELATION;

CELL LINE; CELL SURVIVAL; CROSS-LINKING REAGENTS; HIV INFECTIONS; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 11144356237     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.005     Document Type: Article

References (25)

1. Zhang L., Ramratnam B., Tenner-Racz K., He Y., Vesanen M., Lewin S., Talal A., Racz P., Perelson A., Korber B., Markowitz M., Ho D. N. Engl. J. Med. 340:1999;1605-1613.
2. Furtado M., Callaway D., Phair J., Kunstman K., Stanton J., Macken C., Perelson A., Wolinsky S. N. Engl. J. Med. 340:1999;1614-1622.
3. De Clercq E. Med. Res. Rev. 22:2002;531-565.
4. Mekouar K., Mouscadet J.-F., Desmaële D., Subra F., Leh H., Savouré D., Auclair C., d'Angelo J. J. Med. Chem. 41:1998;2846-2857.
5. Zouhiri F., Mouscadet J.-F., Mekouar K., Desmaële D., Savouré D., Leh H., Subra F., Le Bret M., Auclair C., d'Angelo J. J. Med. Chem. 43:2000;1533-1540.
6. Ouali M., Laboulais C., Leh H., Gill D., Desmaële D., Mekouar K., Zouhiri F., d'Angelo J., Auclair C., Mouscadet J.-F., Le Bret M. J. Med. Chem. 43:2000;1949-1957.
7. Ouali M., Laboulais C., Leh H., Gill D., Xhuvani E., Zouhiri F., Desmaële D., d'Angelo J., Auclair C., Mouscadet J.-F., Le Bret M. Acta Biochim. Pol. 47:2000;11-22.
8. d'Angelo J., Mouscadet J.-F., Desmaële D., Zouhiri F., Leh H. Pathol. Biol. 49:2001;237-246.
9. Burdujan R., d'Angelo J., Desmaële D., Zouhiri F., Tauc P., Brochon J.-C., Auclair C., Mouscadet J.-F., Pernot P., Tfibel F., Enescu M., Fontaine-Aupart M.-P. Phys. Chem. Chem. Phys. 3:2001;3797-3804.
10. Zouhiri F., Desmaële D., d'Angelo J., Ourevitch M., Mouscadet J.-F., Leh H., Le Bret M. Tetrahedron Lett. 42:2001;8189-8192.
11. Polanski J., Zouhiri F., Jeanson L., Desmaële D., d'Angelo J., Mouscadet J.-F., Gieleciak R., Gasteiger J., Le Bret M. J. Med. Chem. 45:2002;4647-4654.
12. For related styrylheterocycles, see: Lee J.Y., Park J.H., Lee S.J., Park H., Lee Y.S. Arch. Pharm. Pharm. Med. Chem. 335:2002;277-282.
13. Yoo H., Lee J.Y., Park J.H., Chung B.Y., Lee Y.S. Il Farmaco. 58:2003;1243-1250.
14. Bader A.R., Kontowicz A.D. J. Am. Chem. Soc. 75:1953;5416-5417.
15. Woodward R.B., Heusler K., Gosteli J., Naegeli P., Oppolzer W., Ramage R., Ranganathan S., Vorbrüggen H. J. Am. Chem. Soc. 88:1966;852.
16. Huang Z.Z., Zhou X.J. Synthesis. 1989;693-694.
17. Sakasai T., Sakamoto T., Yamanaka H. Heterocycles. 13:1979;235-238.
18. Houwing H.A., Van Oene J.C., Horn A.S. Pharm. Weekblad Sci. Ed. 5:1983;177-181.
19. Jurd L. J. Am. Chem. Soc. 81:1959;4606-4610.
20. Bengtsson S., Högtberg T. J. Org. Chem. 54:1989;4549-4553.
21. Shioiri T., Ninomiya K., Yamada S.-I. J. Am. Chem. Soc. 94:1972;6203-6205.
22. Gannett P.M., Nagel D.L., Reilly P.J., Lawson T., Sharpe J., Toth B. J. Org. Chem. 53:1988;1064-1071.
23. Kita Y., Arisawa M., Gyoten M., Nakajima M., Hamada R., Tohma H., Takada T. J. Org. Chem. 63:1998;6625-6633.
24. Guaiacol was used as tert-butyl cation scavenger to prevent the formation of by-products issuing from the recapture of this cation. In this respect, see: Yajima H., Takeyama M., Kanaki J., Nishimura O., Fujino M. Chem. Pharm. Bull. 26:1978;3752-3757.
25. 6) δ 184.2 (C), 170.6 (C), 165.2 (C), 161.0 (C), 150.1 (C), 138.6 (C), 137.7 (CH), 134.2 (C), 133.2 (CH), 132.6 (C), 129.0 (2CH), 128.7 (CH), 128.6 (CH), 127.2 (2CH), 120.5 (CH), 111.8 (C), 93.9 (CH).