Structure-activity relationships in platelet-activating factor. Part 13: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 or pure antiretroviral activity

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 23, 2006, Pages 8109-8125

  Serradji, Nawal ^a   Bensaid, Okkacha ^a,b   Martin, Marc ^c   Sallem, Wafa ^a   Dereuddre Bosquet, Nathalie ^d   Benmehdi, Houcine ^a,b   Redeuilh, Catherine ^a   Lamouri, Aazdine ^a   Dive, Georges ^e   Clayette, Pascal ^d   Heymans, Françoise ^a  

^a Laboratoire de Pharmacochimie   (France)

^b Faculté des Sciences   (Algeria)

^c INSTITUT DE RADIOPROTECTION ET DE SÛRETÉ NUCLÉAIRE   (France)

^d SPI BIO   (France)

^e UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

AIDS dementia complex; Anti HIV 1; Anti PAF; Brain

Indexed keywords

1 BENZYL 2 ETHOXYCARBONYL 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 1 BENZYL 2 HYDROXYMETHYL 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 1 BENZYL 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 (3,4,5 TRIMETHOXYBENZOYL) PIPERAZINE; 1 BENZYL 2 PHENYLOXYCARBONYLOXYMETHYL 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 ETHOXYCARBONYL 1 (3,4,5 TRIMETHOXYBENZOYL) 4 TRIPHENYLMETHYLPIPERAZINE; 2 ETHOXYCARBONYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (4 BUTOXY3,5 DIMETHOXYBENZOYL) 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (4 HYDROXY 3,5 DIMETHOXYBENZOYL) 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 DIPHENYLMETHYL 4 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 (4 HYDROXY 3,5 DIMETHOXYBENZOYL) 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 (4,5 DIHYDRO 5 OXO 1,2,4 4H OXADIAZOL 3 YLMETHYL) 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 (CYANODIPHENYLMETHYL) 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 [PHENYL(PYRIDIN 4-YL)METHYL] 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 N HYDROXYAMIDINOMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 3 ETHOXYCARBONYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIRAZINE; 3 ETHOXYCARBONYL 1 TRIPHENYLMETHYLPIPERAZINE; 3 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL) 4 (METHOXYCARBONYLDIPHENYLMETHYL)PIPERAZINE; 3 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (3,4,5 TRIMETHOXYTHIOBENZOYL) PIPERAZINE; 3 N,N DIETHYLAMINOCARBONYLOXYMETHYL 4 (3,4,5 TRIMETHOXYBENZOYL) 1 (3,4,5 TRIMETHOXYTHIOBENZOYL)PIPERAZINE; 4 BENZYL 2 ETHOXYCARBONYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 4 BENZYL 2 HYDROXYMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 4 BENZYL 2 N,N DIETHYLAMINOCARBONYLOXYMETHY1 (3,4,5 TRIMETHOXYBENZOYL) PIPERAZINE; 4 BENZYL 2 PHENOXYCARBONYLOXYMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; 4 CYANOMETHYL 2 N,N DIETHYLAMINOCARBONYLOXYMETHYL 1 (3,4,5 TRIMETHOXYBENZOYL)PIPERAZINE; ANTIVIRUS AGENT; PIPERAZINE DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ACQUIRED IMMUNODEFICIENCY SYNDROME; ANTI-HIV AGENTS; ANTI-RETROVIRAL AGENTS; DEMENTIA; DOSE-RESPONSE RELATIONSHIP, DRUG; HIV-1; HUMANS; PIPERAZINES; PLATELET ACTIVATING FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33751043926     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.07.031     Document Type: Article

References (29)

1. Lipton S.A., and Gendelman H.E. N. Eng. J. Med. 332 (1995) 934-940
2. Brew B.J. Neurol. Clin. 17 (1999) 861-881
3. Brodt H.R., Kamps B.S., Gute P., Knupp B., Staszewski S., and Helm E.B. AIDS 11 (1997) 1731
4. Sacktor N., Lyles R.H., Skolasky R., Kleeberger C., Selnes O.A., Miller E.N., Becker J.T., Cohen B., and McArthur J.C. Neurology 56 (2001) 257
5. Wiley C.A., Schrier R.D., Nelson J.A., Lampert P.W., and Oldstone M.B. Proc. Natl. Acad. Sci. U.S.A. 83 (1986) 7089-7093
6. Giulian D., Vaca K., and Noonan C.A. Science 250 (1990) 1593-1596
7. Pulliam L., Herndier B.G., Tang N.M., and McGrath M.S. J. Clin. Invest. 87 (1991) 503-512
8. Bernton E.W., Bryant H.U., Decoster M.A., Orenstein J.M., Ribas J.L., Meltzer M.S., and Gendelman H.E. AIDS Res. Hum. Retroviruses 8 (1992) 495-503
9. Genis P., Jett M., Bernton E.W., Boyle T., Gelbard H.A., Dzenko K., Keane R.W., Resnick L., Mizrachi Y., Volsky D.J., Epstein L.G., and Gendelman H.E. J. Exp. Med. 176 (1992) 1703-1718
10. Gelbard H.A., Nottet H.S.L., Swindells S., Jett M., Dzenko K.A., Genis P., White R., Wang L., Choi Y.-B., Zhang D., Lipton S.A., Tourtelotte W.W., Epstein L.G., and Gendelman H.E.. J. Virol. 68 (1994) 4628-4635
11. Perry S.W., Hamilton J.A., Tjoelker L.W., Dbaibo G., Dzenko K.A., Epstein L.G., Hannun Y., Whittaker J.S., Dewhurst S., and Gelbard H.A. J. Biol. Chem. 273 (1998) 17660-17664
12. Serradji N., Bensaid O., Martin M., Kan E., Dereuddre-Bosquet N., Redeuilh C., Huet J., Heymans F., Lamouri A., Clayette P., Dong C.-Z., Dormont D., and Godfroid J.-J. J. Med. Chem. 43 (2000) 2149-2154
13. Martin M., Serradji N., Dereuddre-Bosquet N., Le Pavec G., Fichet G., Lamouri A., Heymans F., Godfroid J.-J., and Dormont D. Antimicrob. Agents Chemother. 44 (2000) 3150-3154
14. Serradji N., Martin M., Bensaid O., Cisternino S., Rouselle C., Dereuddre-Bosquet N., Huet J., Redeuilh C., Lamouri A., Dong C.-Z., Clayette P., Scherrmann J.-M., Dormont D., and Heymans F. J. Med. Chem. 47 (2004) 6410-6419
15. Jucker E., and Rissi E. Helv. Chim. Acta 45 (1962) 2383-2402
16. Lamouri A., Heymans F., Tavet F., Dive G., Batt J.-P., Blavet N., Braquet P., and Godfroid J.-J. J. Med. Chem. 36 (1993) 990-1000
17. Yde B., Yousif N.M., Pedersen U., Thomsen I., and Lawesson S.O. Tetrahedron 40 (1984) 2047-2052
18. Scheibye S., Pedersen B.S., and Lawesson S.O. Bull. Soc. Chim. Belg. 87 (1978) 229-238
19. Kohara W., Kubo K., Imamiya E., Wada T., Inada Y., and Naka T. J. Med. Chem. 39 (1996) 5228-5235
20. Tetko I.V., and Tanchuk V.Y. J. Chem. Inf. Comput. Sci. 42 (2002) 1136
21. Tetko I.V., Tanchuk V.Y., and Villa A.E. J. Chem. Inf. Comput. Sci. 41 (2001) 1407
22. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., and Prokopenko V.V. J. Comput. Aid. Mol. Des. 19 (2005) 453
23. Lamotte-Brasseur J., Heymans F., Dive G., Lamouri A., Redeuilh C., Hosford D., Braquet P., and Godfroid J.-J. Lipids 26 (1991) 1167-1171
24. Dive G., Godfroid J.-J., Lamotte-Brasseur J., Batt J.-P., Heymans F., Dupond L., and Braquet P. J. Lipid Mediators 1 (1989) 201-215
25. Heymans F., Dive G., Lamouri A., Bellahsene T., Touboul E., Huet J., Tavet F., Redeuilh C., and Godfroid J.-J. J. Lipid Mediators Cell Signal. 15 (1997) 161-173
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA, 1998.
27. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
28. Tavet F., Lamouri A., Heymans F., Dive G., Touboul E., Blavet N., and Godfroid J.-J. J. Lipid Mediators Cell Signal. 15 (1997) 145-159
29. Cazenave J.P., Benveniste J., and Mustard J.F. Lab. Invest. 41 (1979) 275-285