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
Dive, Georges ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Batt, Jean-Pierre
Blavet, Nicole
Braquet, Pierre
Godfroid, Jean-Jacques
Language :
English
Title :
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
Publication date :
1993
Journal title :
Journal of Medicinal Chemistry
ISSN :
0022-2623
eISSN :
1520-4804
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Benveniste, J.; Henson, P. M.; Cochrane, C. G. Leukocyte Dependent Histamine Release from Rabbit Platelets: The Role of IgE, Basophils and a Platelet Activating Factor. J. Exp. Med. 1972, 136, 1356–1377.
Benveniste, J. Characteristics and Purification of a Platelet Activating Factor from Human and Rabbit Leukocytes. Fed. Proc. 1974, 33, 797.
Benveniste, J. Platelet Activating Factor, a New Mediator of Anaphylaxis and Immune Complex Deposition from Rabbit and Human Basophils. Nature (London) 1974, 249, 581–582.
Demopoulous, C. A.; Pinckard, R. N.; Hanahan, D. J. Platelet Activating Factor. Evidence for 1-O-alkyl-sn-glyceryl-3-phosphorylcholine as the Active Component (a New Class of Lipid Chemical Mediators). J. Biol. Chem. 1979, 254, 9355–9358.
Blank, M. L.; Snyder, F.; Byers, L. W.; Brooks, B.; Muirhead, E. E. Antihypertensive Activity of an Alkyl Analog of Phosphatidylcholine. Biochem. Biophys. Res. Commun. 1979, 90, 1194–1200.
Benveniste, J.; Tencé, M.; Varenne, P.; Bidault, J.; Boullet, C.; Polonsky, J. Semi-synthesis and Proposed Structure of Platelet-Activating Factor (PAF): PAF-acether an Alkyl Ether Analog of Lysophosphatidylcholine. C. R. Acad. Sci. (Paris) 1979, 289, 1037–1040.
Godfroid, J. J.; Heymans, F.; Michel, E.; Redeuilh, C.; Steiner, E.; Benveniste, J. Platelet Activating Factor (PAF-acether): Total Synthesis of 1-o-octadecyl-2-O-acetyl-sn-glycero-3-phosphorylcholine. FEBS Lett. 1980, 116, 161–164.
Heymans, F.; Michel, E.; Borrel, M. C.; Wichrowski, B.; Godfroid, J. J. New total synthesis of PAF-acether and of its enantiomer. CR. Acad. Sci. (Paris) 1981, 293, 49–52.
Heymans, F.; Michel, E.; Wichrowski, B.; Godfroid, J. J.; Convert, O.; Coeffier, E.; Tencé, M.; Benveniste, J. New Total Synthesis and High Resolution 1H NMR Spectrum of Platelet Activating Factor, its Enantiomer and Racemic Mixtures. Biochim. Biophys. Acta 1981, 666, 230–237.
Borrel, M.-C.; Broquet, C.; Heymans, F.; Michel, E.; Redeuilh, C.; Wichrowski, B.; Godfroid, J.J. Additional Techniques for the Total Synthesis of PAF-acether. Agents Actions 1982, 12, 709–710.
Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S.; Ohno, M. An Efficient and Stereoselective Synthesis of Platelet-Activating Factor and the Enantiomers from D- and L-Tartaric Acids. Tetrahedron Lett. 1982, 23, 3507–3510.
Vargaftig, B. B.; Braquet, P. PAF-acether Today: Relevance for Acute Experimental Anaphylaxis. Br. Med. Bull. 1987, 43, 312–335.
Braquet, P.; Touqui, L.; Shen, T. Y.; Vargaftig, B. B. Perspectives in Platelet Activating Factor Research. Pharmacol. Rev. 1987, 39, 97–145.
Venuti, M. C. PlateletActivatingFactor: Multi-faceted Biochemical and Physiological Mediator. Annu. Rep. Med. Chem. 1985, 20, 193–202.
Snyder, F. Chemical and Biochemical Aspects of Platelet Activating Factor: A Novel Class of Acetylated Ether-linked Choline-phospholipids. Med. Res. Rev. 1985, 5, 107–140.
Snyder, F. Platelet Activating Factor (PAF), a Novel Type of Phospholipid with Diverse Biological Properties. Annu. Rep. Med. Chem. 1982, 17, 243–252.
Winslow, C. M., Lee, M. L., Eds. New Horizons in Platelet Activating Factor Research; John Wiley and Sons: New York, 1987.
Snyder, F., Ed. Platelet Activating Factor and Related Lipid Mediators; Plenum Press: New York, 1987.
Barnes, P. Y., Page, C. P., Henson, P. M., Eds. Platelet Activating Factor and Human Diseases; Blackwell Sc. Publ.: Oxford, 1989.
Handley, D. A., Saunders, R. N., Houlihan, W. J., Tomesch, J. C., Eds. Platelet Activating Factor in Endotoxin and Immune Diseases; Marcel Dekker, Inc.: New York, 1990.
Godfroid, J. J.; Braquet, P. PAF-acether Specific Binding Sites. 1. Quantitative SAR study of PAF-acether isosteres. Trends Pharmacol. Sci. 1986, 7, 368–373.
Braquet, P.; Godfroid, J. J. PAF-acether Specific Binding Sites. 2. Design of Specific Antagonists. Trends Pharmacol. Sci. 1986, 7, 397–403.
Chang, M. N. PAF and PAF Antagonists. Drugs Future 1986, 11, 869–875.
Braquet, P.; Godfroid, J. J. Conformational Properties of the PAF-acether Receptor on Platelets Based on Structure-activity Studies. In Platelet Activating Factor and Related Lipid Mediators; Snyder, F., Ed.; Plenum Press: New York, 1987; pp 191–235.
Saunders, R. N.; Handley, D. A. Platelet Activating Factor Antagonists. Annu. Rev. Pharmacol. Toxicol. 1987, 27, 237–255.
Hanahan, D. J.; Kumar, R. Platelet Activating Factor; Chemical and Biochemical characteristics. Prog. Lipid Res. 1987, 27, 237–255.
Shen, T. Y.; Hwang, S. B.; Doebber, T. W.; Robbins, J. C. The Chemical and Biological Properties of PAF Agonists, Antagonists and Biosynthetic Inhibitors. In Platelet Activating Factor and Related Lipid Mediators; Snyder, F., Ed.; Plenum Press: New York, 1987; pp 153–190.
Handley, D. A. Development and Therapeutic Indications for PAF Antagonists. Drugs Future 1988, 13, 137–152.
Hosford, D.; Page, C. P.; Barnes, P. J.; Braquet, P. PAF-receptor Antagonists. In Platelet-Activating Factor and Human Diseases; Barnes, J. P., Page, C. P., Henson, P. M., Eds.; Blackwell Scientific Publications: Oxford, 1989; pp 82–116.
Houlihan, W.J. Platelet-Activating Factor Antagonists. In Platelet-Activating Factor in Endotoxin and Immune Diseases; Handley, D. A., Saunders, R. N., Houlihan, W. J., Tornesch, J. C., Eds.; Marcel Dekker, Inc.: New York, 1990; pp 31–75.
Dive, G.; Godfroid, J.-J.; Lamotte-Brasseur, J.; Batt, J.-P.; Heymans, F.; Dupont, L.; Braquet, P. J. Lip. Med. 1989, 1, 201–215.
Godfroid, J. J.; Dive, G.; Lamotte-Brasseur, J.; Batt, J. P.; Heymans, F. PAF-Receptor Structure: a Hypothesis. Lipids 1991, 26, 1162–1166.
Lamotte-Brasseur, J.; Heymans, F.; Dive, G.; Lamouri, A.; Redeuilh, C.; Hosford, D.; Braquet, P.; Godfroid, J. J. PAF-Receptor and “Cache-oreilles” effect. Simple PAF antagonists. Lipids 1991, 26, 1167–1171.
Jucker, E.; Rissi, E. Synthetic medicinals. X. On C-substituted Piperazine Derivative. Helv. Chim. Acta 1962, 45, 2383–2402.
Jaeger, D. A.; Broadhurst, M. D.; Cram, D. J. Electrophilic Substitution at Saturated Carbon. 52. A Model for the Proton Transfer of Biological Transamination and the Effect of a 4-Pyridyl Group on the Base-Catalyzed Racemization of a Carbon Acid. J. Am. Chem. Soc. 1979, 101, 717–732.
Toldy, L.; Toth, I.; Borsy, J. Derivatives of Piperazine. I. Derivatives of 3,4,5-Trimethoxybenzoyl Piperazine, a New Group of Compounds with antiulcerogenic Activity. Acta Chim. Acad. Sci. Hung. 1966, 49, 265–286.
Irikura, T.; Masuzawa, K.; Nishino, K.; Kitagawa, M.; Uchida, H.; Ichinoseki, N.; Ito, M. New Analgetic Agents. V. l-Butyryl-4-cinnamylpiperazine Hydrochlorid and Related compounds. J. Med. Chem. 1968, 11, 801–804.
Benington, F.; Morin, R. D.; Clark, Leland C., Jr. Mescaline analogs. IV. Substituted 4,5,6-Trimethoxyindoles. J. Org. Chem. 1955, 20, 1454–1457.
Ninomiya, K.; Shioiri, T.; Yamada, S. Phosphorus in Organic Synthesis. VII. Diphenyl Phosphorazidate (DPPA). A new convenient reagent for a modified Curtius Reaction. Tetrahedron 1973, 30, 2151–2157.
Allen, C. F. H.; Bell, A. Undecyl Isocyanate. In Organic Syntheses; Horning, E. C., Ed.; John Wiley and Sons: New York, 1955; Collect. Vol. III, pp 846–847.
Takatani, M.; Yoshioka, Y.; Tasala, A.; Terashita, Z.; Imura, Y.; Nishikawa, K.; Tsushima, S. Platelet-Activating Factor Antagonists: Synthesis and Structure-Activity Studies of Novel PAF Analogues Modified in the Phosphorylcholine Moiety. J. Med. Chem. 1989, 32, 56–64.
Godfroid, J. J.; Broquet, C.; Jouquey, S.; Lebbar, M.; Heymans, F.; Redeuilh, C.; Steiner, E.; Michel, E.; Coeffier, E.; Fichelle, J.; Worcel, M. Structure-Activity Relationship in Paf-acether 3. Hydrophobic Contribution to Agonistic Activity. J. Med. Chem. 1987, 30, 792–797.
Olansky, L.; Moncrief, J. W. N-N′-Bis-(3-bromopropionyl) piperazine. Acta Crystallogr. 1973, B29, 357–360.
Tien-Ming, K.; Moncrief, J. W. N-N'-Bis-(3-chloropropionyl) piperazine. Acta Crystallogr. 1975, B31, 2544–2546.
Rekker, R. F.; de Koort, M. M. The Hydrophobic Fragmental Constant; Extension to a 1.000 data Point Set. Eur. J. Med. Chem.-Chim. Ther. 1979, 14, 479–488.
Heuer, H. O. Web 2347: Pharmacology of a New Very Potent and Long Acting Hetrazepinoic PAF-Antagonist and its Action in Repeatedly sensitized Guinea-Pigs. J. Lipid Med. 1991, 4, 39–44.
Birke, F. Oral communication at the 1st Med. Chem. Co., Frankfurt (Germany), May 9–12, 1991.
Favre, E.; Heymans, F.; Redeuilh, C.; Batt, J. P.; Massicot, F.; Blavet, N.; Braquet, P.; Godfroid, J. J. Structure-Activity Relationships in Platelet-Activating Factor (PAF-antagonists) 6. Synthesis and in vitro Antagonistic Activities of 2-substituted 5-ox-otetrahydrofurans. J. Lipid Med. 1992, 5, 23–40.
Hwang, S. B.; Lam, M. H.; Alberts, A. W.; Chabala, J. C.; Ponpipom, M. M. Biological and Pharmacological Characterization of L-659, 989: an Extremly Potent, Selective and Competitive Receptor Antagonist of PAF. J. Pharmacol. Ther. 1988, 246, 534–541.
Kellie, G. M.; Riddel, F. G. Non-Chair Conformations of Six-Membered Rings. In Topics in Stereochemistry; Allinger, N. L., Elliel, E. L., Eds.; Intersciences: New York, 1974; Vol. 8, pp 225–269.
Tsuboyama, S.; Tsuboyama, K.; Uzawa, J.; Koda, R.; Nakamaru, M.; Kobayashi, K.; Sakurai, T. Conformation of 1,4-dibenzoyl-2,5-dialkylpiperazine. Twist-boat Ring Conformation. Tetrahedron Lett. 1977, 2895–2898.
Sakurai, T.; Nakamaru, M.; Tsuboyama, S.; Tsuboyama, K. (R,S)-1,4-dibenzoyl-cis-2,5-dimethylpiperazine. Acta Crystallogr. 1977, B33, 3568–3571.
Hiramatsu, M.; Sakurai, T.; Tsuboyama, S.; Tsuboyama, K. (S)-1,4-dibenzoyl-cis-2,5-dimethylpiperazine. Acta Crystallogr. 1978, B34, 3469–3471.
Stensland, B.; Batt, J. P.; Lamouri, A.; Godfroid, J. J. Platelet-Activating Factor Antagonists. Structure of N,N′-Bis(3,4,5-Trimethoxybenzoyl)-2-Piperazinylmethyl 2,2-Dimethylpropanoate. Acta Crystallogr. 1991, C47, 1453–1457.
Wichrowski, B.; Jouquey, S.; Broquet, C.; Heymans, F.; Godfroid, J. J.; Worcel, M. Structure-Activity Relationship in PAF-acether. 4. Synthesis and Biological Activities of Carboxylate Isosteres. J. Med. Chem. 1988, 31, 410–415.
Corey, E. J.; Parry, M. J.; Chung-Pin Chen. Dual Binding Modes to the Receptor for Platelet Activating Factor (PAF) of anti-PAF trans-2,5-diarylfurans. Tetrahedron Lett. 1988, 29, 2899–2902.
Larock, R. C.; Gong, W. H. Palladium-Catalyzed Synthesis of trans-2,5-Diaryltetrahydrofurans, Potent Platelet-Activating Factor Antagonists. J. Org. Chem. 1990, 55, 407–408.
Shen, T. Y. Chemical and Biochemical Characterization of Lignan Analogs as Novel PAF-Receptor Antagonists. Lipids 1991, 26, 1154–1156.
Guthrie, R. W.; Kaplan, G. L.; Mennona, F. A.; Tilley, J. W.; Kierstead, R. W.; Mullin, J. G.; Le Mahieu, R. A.; Zawoiski, S.; O'Donnel, M.; Crowley, H.; Yaremko, B.; Welton, A. F. Pentedienyl Carboxamide Derivatives as Antagonists of Platelet-Activating Factor. J. Med. Chem. 1989, 32, 1820–1835.
Robant, C.; Durand, G.; James, C.; Lavé, D.; Sédivy, P.; Floch, A.; Mondot, S.; Pacot, D.; Cavero, I.; Le Fur, G. PAF Binding Sites. Characterization by [3H] 52,770 RP, a Pyrrolo [1,2-c] Thiazole Derivative in Rabbit Platelets. Biochem. Pharmacol. 1987, 36, 3221–3229.
Cazals-Stenzel, J. Thiene-triazolo-1,4-diazepines as Antagonists of Platelet-Activating Factor: Present Status. Lipids 1991, 26, 1157–1161.
Tencé, M.; Coeffier, E.; Heymans, F.; Godfroid, J. J.; Benveniste, J. Structural Analogs of Platelet-Activating Factor (PAF-acether). Biochimie 1981, 63, 723–727.
Godfroid, J. J.; Dive, G. PAF-receptor Agonists. In Platelet Activating Factor and Immune Diseases; Handley, U. A., Saunders, R. N., Houlihan, W. J.; Tomesch, J. C., Eds.; Marcel Dekker, Inc.: New York, 1990; pp 15–30.
Batt, J. P.; Lamouri, A.; Tavet, F.; Heymans, F.; Dive, G.; Godfroid, J. J. New Hypothesis on the Conformation of the PAF-Receptor from Studies on the Geometry of Selected Platelet-Activating Factor-Antagonists. J. Lipid Med. 1991, 4, 343–346.
Telley, J. W.; Clader, J. W.; Zawoiski, S.; Wirkus, M.; Le Mahieu, R. A.; O'Donnel, M.; Growley, M.; Weton, A. F. Biphenylcarboxamide Derivatives as Antagonists of Platelet-Activating Factor. J. Med. Chem. 1989, 32, 1814–1820.
Shimazaki, N.; Shima, I.; Okamoto, M.; Yoshida, K.; Hemmi, K.; Hashimoto, M. Paf Inhibitory Activity of Diketopiperazines: Structure-Activity Relationships. Lipids 1991, 26, 1175–1178.
Lamotte-Brasseur, J.; Dive, G.; Lamouri, A.; Heymans, F.; Godfroid, J. J. PAF-Receptor. 3. Conformational and Electronic Properties of PAF-like Agonists and Antagonists. Biochim. Biophys. Acta 1991, 1085, 91–105.
Honda, Z.-I.; Nakamura, M.; Miki, J.; Minami, M.; Watanabe, T.; Seyama, Y.; Okado, H.; Toch, H.; Ito, K.; Miyamoto, T.; Shimizu, T. Cloning by Functional Expression of Platelet-Activating Factor Receptor from Guinea-pig Lung. Nature 1991, 349, 342–346.
Valone, F. H. PAF-binding to Specific Cell Membrane Receptors. In Platelet-Activating Factor and Related Lipid Mediators; Snyder, F., Ed.; Plenum Press: New York, 1987; pp 137–151.
Hwang, S. B. Specific Receptors of Platelet-Activating Factor, Receptor Heterogeneity and Signal Transduction Mechanisms. J. Lipid Med. 1990, 2, 123–158.
Hwang, S. B. Identification of a second Putative Receptor of Platelet-Activating Factor from Human Polymorphonuclear Leukocytes. J. Biol. Chem. 1988, 263, 3225–3233.
Stewart, A. G.; Grigoriadis, G. Structure-Activity Relationships for Platelet-Activating Factor (PAF) and Analogues Reveal Differences between PAF-Receptors on Platelets and Macrophages. J. Lipid Med. 1991, 4, 299–308.
Hodgkin, E. E.; Miller, A.; Whittaker, M. A Partial Pharmacophore for the Platelet Activating Factor (PAF) Receptor. Bioorg. Med. Chem. Lett. 1992, 2, 597–602.
Cazenave, J. P.; Benveniste, J.; Mustard, J. F. Aggregation of Rabbit Platelets by Platelet-Activating Factor is Independent of the Release Reaction and the Arachidonate pathway and Inhibited by Membrane-Active Drugs. Lab. Invest. 1979, 41, 275–285.
Domingo, M. T.; Chabrier, P. E.; Thiberghin, C.; Wisner, A.; Dray, F.; Braquet, P. Inhibition by Ginkgolides of the Binding of [3H]-PAF Platelet Activating Factor (PAF) to Platelet Membranes. In Ginkgolides: chemistry, biology, pharmacology and clinical perspectives; Braquet, P., Ed.; J. R. Prous Science: Barcelona, 1988; Vol. 1, pp 79–84.
Allinger, N. L. MM-2 (77). Quantum Chemistry Exchange, Department of Chemistry Indiana University, Bloomington, IN 47405.
Dewar, M. J. S.; Zoebisch, E. G.; Hearly, E. F.; Steward, J. P. P. A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902–3909.
Giessner-Prettre, C.; Pullmann, A. Molecular Electrostatic Potentials: Comparison between ab initio and CNDO Results. Theor. Chim. Acta (Berlin) 1972, 25, 83–88.
Pople, J. A.; Beveridge, D. L. Approximate Molecular Orbital Theory; MacGraw-Hill: New York, 1970.
Peeters, D.; Sana, M. Program DENPOT, University of Louvain, Louvain-La-Neuve, Belgium, QCPE 360. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN 47405.
Jorgensen, W. L. Program PSI 77, Purdue University, West Lafayette, QCPE 340. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN 47405.
