Design and modeling of new platelet-activating factor antagonists.2. Synthesis and biological activity of 1,4-bis-(3',4',5'-trimethoxybenzoyl)-2-alkyl and 2-alkoxymethylpiperazines
Dive, Georges ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Touboul, Estéra
Blavet, Nicole
Godfroid, Jean-Jacques
Language :
English
Title :
Design and modeling of new platelet-activating factor antagonists.2. Synthesis and biological activity of 1,4-bis-(3',4',5'-trimethoxybenzoyl)-2-alkyl and 2-alkoxymethylpiperazines
Barnes, P.Y., Page, C.P. and Henson, P.M., (Eds.), (1989) Platelet Activating Factor and Human Diseases.Blackwell, Oxford.
Batt, J.-P., Lamouri, A., Tavet, F., Heymans, F., Dive, G. and Godfroid, J.-J. (1991) New hypothesis on the conformation of the PAF-receptor from studies on the geometry of selected platelet-activating factor-antagonists.J. Lipid Mediators 4, 343-346.
Behun, J. and Levine, R. (1961) The chemistry of pyrazine and its derivatives. IV. The alkylation and arylation of methylpyrazine. J. Am. Chem. Soc. 26, 3379-3382.
Bernady, K.F., Floyd, M.B., Poletto, J.F. and Weiss, M.J. (1979) Prostaglandins and congeners. 20. Synthesis of prostaglandins via conjugate addition of lithium trans-1-alkenyltrialkylalanate reagents. A novel reagent for conjugate 1,4-additions. J. Org. Chem. 44, 1438-1447.
Braquet, P., Touqui, L., Shen, T.Y. and Vargaftig, B.B. (1987) Perspectives in platelet-activating factor research.Pharmacol. Rev. 39, 97-145.
Corey, E.J., Niwa, H. and Knolle J. (1978) Total Synthesis of (S)-12-Hydroxy-5,8,14-cis,10-trans-ei-cosatetraenoic acyl (Samuelsson's HETE).J. Am. Chem. Soc. 100, 1942-1943.
Dive, G., Godfroid, J.-J., Lamotte-Brasseur, J. et al. (1989) PAF-receptor. I. "Cache-oreilles" effect of selected high potency platelet-activating factor (PAF) antagonist. J. Lipid Mediators. 1, 201-215.
Godfroid, J.J., Broquet, C., Jouquey, S. et al. (1987) Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity. J. Med. Chem. 30, 792-797.
Godfroid, J.-J., Dive, G., Lamotte-Brasseur, J., Batt, J.-P. and Heymans, F. (1991) PAF-receptor structure: a hypothesis.Lipids 26, 1167-1171.
Handely, D.A., Saunders, R.N., Houlihan, W.J. and Tomesch, J.C., (Eds.), (1990) Platelet Activating Factor in Endotoxin and Immune Diseases, Marcel Dekker, New York.
Hansch, C., Leo, A. and Hoekman, D. (1990) Exploring QSAR, Hydrophobic, Electronic, and Steric Constants.In: Heller, S.R., (Ed.), ACS Professional Reference Book, American Chemical Society, Washington.
Heymans, F., Steiner, E., Jouquey, S. and Godfroid, J.J. (1989) PAF-receptor.2. Quantitative hydrophobic contribution of the agonist's etheroxid chain. J. Lipid Mediators 1, 303-312.
Jucker, E. and Rissi, E. (1962) Synthetic medicinals. X. On C-substituted piperazine derivative. Helv. Chim. Acta 45, 2383-2401.
Koltai, M., Guinot, P., Hosford, D. and Braquet, P. (1994) Platelet-activating factor antagonists; scientific background and possible clinical applications.Adv. Pharmacol. 28, 81-167.
Kubinyi, H. (1976) Quantitative structure-activity relationships. IV-Non-linear dependence of biological activity on hydrophobic character: a new model. Arzneim. Forsch. 26, 1991-1997.
Kubinyi, H. (1977) Quantitative structure-activity relationships. 7. The bilinear model, a new model for nonlinear dependence of biological activity on hydrophobic character. J. Med. Chem. 20, 625-629.
Lamotte-Brasseur, J., Heymans, F., Dive, G. et al. (1991) PAF-Receptor and "Cache-oreilles" effect. Simple PAF antagonists. Lipids 26, 1167-1171.
Lamouri, A., Heymans, F., Tavet, F. et al. (1993) Design and modeling of new platelet-activating factor antagonists. 1. Synthesis and biological activity of 1,4-bis-(3′,4′,5′-trimethoxybenzoyl)-2-[[(substituted carbonyl and carbamoyl)oxy]methyl]-piperazines. J. Med. Chem. 36, 990-1000.
McFarland, J.W. (1970) On the parabolic relationship between drug potency and hydrophobicity.J. Med. Chem. 13, 1192-1196.
Pennitson, J. T., Beckett, L., Bentley, D. L. and Hansch, C. (1969) Passive permeation of organic compounds through biological tissue; a non-steady-state theory.Mol. Pharmacol. 5, 333-341.
Rekker, R. F. and De Koort, M. M. (1979) The hydrophobic fragmental constant; extension to a 1000 data point set.Eur. J. Med. Chem.-Chim. Ther. 14, 479-488.
Snyder, F. (1982) Platelet activating factor (PAF), a novel type of phospholipid with diverse biological properties.Annu. Rep. Med. Chem. 17, 243-252.
Snyder, F. (1985) Chemical and biochemical aspects of platelet-activating factor.A novel class of acetylated ether-linked choline-phospholipids. Med. Res. Rev. 5, 107-140.
Snyder, F., (Ed.), (1987) Platelet Activating Factor and Related Lipid Mediators, Plenum, New York, 1987.
