Design of new potent and selective secretory phospholipase A2 inhibitors. Part 5: Synthesis and biological activity of 1-alkyl-4-[4,5-dihydro-1,2,4-[4H]-oxadiazol-5-one-3-ylmethylbenz-4′-yl(oyl)] piperazines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 3, 2008, Pages 1242-1253

  Boukli, Latifa ^a   Touaibia, Mohamed ^a   Meddad Belhabich, Nadia ^a   Djimdé, Atimé ^a   Park, Chang Ha ^b   Kim, Jung Joo ^b   Yoon, Joo Hyoung ^b   Lamouri, Aazdine ^a   Heymans, Françoise ^a  

^a Laboratoire de Pharmacochimie   (France)

^b Yang Ji Chemical Co Ltd   (South Korea)

Author keywords

A2 inhibitors; Indomethacin; Phospholipase; Piperazine; Relationships; Structure activity

Indexed keywords

1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YL]BENZOYL] 4 TETRADECYLPIPERAZINE; 1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YL]BENZYL] 4 TETRADECYLPIPERAZINE; 1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YLETHYL]BENZOYL] 4 TETRADECYLPIPERAZINE; 1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YLMETHYL]BENZYL] 4 TETRADECYLPIPERAZINE; 1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YLMETHYL]PHENYL 4 OCTADECYLPIPERAZINE; 1 [4 [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YLPROPYL]BENZOYL] 4 TETRADECYLPIPERAZINE; 1 [4' [4,5 DIHYDRO 1,2,4 (4H) 5 OXO OXADIAZOL 3 YLMETHYL]BENZOYL] 4 OCTADECYLPIPERAZINE; CARRAGEENAN; INDOMETACIN; LY 311727; PHOSPHOLIPASE A2; PHOSPHOLIPASE A2 INHIBITOR; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; FLUOROMETRY; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PAW EDEMA; RAT; SKIN INFLAMMATION; STRUCTURE ACTIVITY RELATION;

ALKYLATION; ANIMALS; BENZENE; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDROGEN; METHYLATION; MOLECULAR STRUCTURE; OXAZOLES; PHOSPHOLIPASES A2, SECRETORY; PIPERAZINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

RATTUS;

EID: 38849126259     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.077     Document Type: Article

References (33)

1. Murakami M., and Kudo I. J. Biochem. (Tokyo) 131 (2002) 285
2. Harris S.G., Padilla J., Koumas L., Ray D., and Phipps R.P. Trends Immunol. 23 (2002) 144
3. Murakami M., and Kudo I. Adv. Immunol. 77 (2001) 163
4. Valentin E., and Lambeau G. Biochim. Biophys. Acta. 1488 (2000) 59
5. Laye, J. P.; Gill, J. H. Therapeutic Focus, DDT, 2003; Vol. 8, No. 15, p 710.
6. Balsinde J., and Dennis E.A. J. Biol. Chem. 271 (1996) 6758
7. Bomalaski J.S., and Clark M.A. Arthritis Rheum. 36 (1993) 190
8. Vadas P. Biochim. Biophys. Acta 1346 (1997) 193
9. Baur M., Schmid O., and Landauer B. Klin. Wochenschr. 67 (1989) 196
10. Uhl W., Büchler M., Nevalainen T.J., Deller A., and Beger H.G. J. Trauma 30 (1990) 1285
11. Büchler M., Deller A., Malfertheiner P., Kleine H.O., and Uhl W. Klein. Wochenschr. 67 (1989) 217
12. Uhl W., Beger H.G., Hoffman G., Hanisch E., Schild A., Waydhas C., Entholzner E., Muller Kellermann W., and Vogeser M. J. Am. Coll. Surg. 180 (1995) 323
13. Büchler M., Malfertheiner P., Schädlich H., Nevalainen T.J., Fress H., and Berger H.G. Gastroenterology 97 (1989) 1521
14. Bird N.C., Goodman A.J., and Johnson A.G. Br. J. Surg. 76 (1989) 731
15. Kortesuo P.T., Nevalainen T.J., Büchler M., and Uhl W. Eur. J. Clin. Chem. Clin. Biochem. 30 (1992) 263
16. Marks F., Muller-Decker K., and Furstenberger G. Toxicology 153 (2000) 11
17. Tapiero H., Ba G.N., Couvreur P., and Tew K.D. Biomed. Pharmacother. 56 (2002) 215
18. Uhl W., Schrag H., Schmitter J.N., and Aufenanger J. Br. J. Surg. 85 (1998) 618
19. Binisti C., Assogba L., Touboul E., Mounier C., Huet J., Ombetta J.E., Dong C.-Z., Redeuilh C., Heymans F., and Godfroid J.-J. Eur. J. Med. Chem. 36 (2001) 809
20. Dillard R.D., Bach N.J., Draheim S.E., Berry D.M., Carlson D.G., Chirgadze N.Y., Clawson D.K., Hartley L.W., Johnson L.M., Jones N.D., McKinney E.R., Mihelich E.D., Olkowski J.L., Schevitz R.W., Smith A.C., Snyder D.W., Sommers C., and Wery J.-P. J. Med. Chem. 39 (1996) 5137
21. Dillard R.D., Bach N.J., Draheim S.E., Berry D.M., Carlson D.G., Chirgadze N.Y., Clawson D.K., Hartley L.W., Johnson L.M., Jones N.D., McKinney E.R., Mihelich E.D., Olkowski J.L., Schevitz R.W., Smith A.C., Snyder D.W., Sommers C., and Wery J.-P. J. Med. Chem. 39 (1996) 5119
22. Maguire A.R., Plunkett S.J., Papot S., Clynes M., O'Connor R., and Touley S. Bioorg. Med. Chem. 9 (2001) 745
23. Glaser K.B. Adv. Pharmacol. 32 (1995) 31
24. Assogba L., Ahamada-Himidi A., Meddad-Bel Habich N., Aoun D., Boukli L., Massicot F., Mounier C., Huet J., Lamouri A., Ombetta J.-E., Godfroid J.-J., Dong C.-Z., and Heymans F. Eur. J. Med. Chem. 40 (2005) 850
25. Dong C.-Z., Ahamada-Himidi A., Plocki S., Aoun D., Touaibia M., Meddad-Bel Habich N., Huet J., Redeuilh C., Ombetta J.-E., Godfroid J.-J., Massicot F., and Heymans F. Bioorg. Med. Chem. 13 (2005) 1989
26. Plocki S., Aoun D., Ahamada-Himidi A., Tavarès-Camarinha F., Dong C.-Z., Massicot F., Huet J., Adolphe-Pierre S., Chau F., Godfroid J.-J., Gresh N., Ombetta J.-E., and Heymans F. Eur. J. Org. Chem. (2005) 2747
27. Jerzy R., Pietraseiwick M., Duszynska B., and Cegla M.T. J. Med. Chem. 35 (1992) 2369
28. Newman A.H., Kline R.H., Allen A.C., Izenwasser S., Clifford G., and Katz J.L. J. Med. Chem. 38 (1995) 3933
29. Brouard, C; Dupont, B.; Leroy, J. M.; Sito, J. P. Ger. Offen. 1975, Deutsches Patent No. GWXXBX DE, 243809, 19750220.
30. Kitamura S., Fukushi H., Miyawaki T., Kawamura M., Konishi N., Terashita Z., and Naka T. J. Med. Chem. 44 (2001) 2438
31. Poi M.J., Tomaszewski J.W., Dunlap C.Y.C.A., Andersen N.H., Gelb M.H., and Tsai M.-D. J. Mol. Biol. 329 (2003) 997
32. Radvanyi F., Jordan L., Russo-Marie F., and Bon C. Anal. Biochem. 117 (1989) 103
33. Rekker R.F., and De Kort H.M. Eur. J. Med. Chem. 14 (1979) 479