The design of dual-acting compounds with PAF receptor antagonistic and 5-lipoxygenase inhibitory activities

Drugs of the Future

Volumn 21, Issue 9, 1996, Pages 933-944

  Hussoin, Md Sajjat ^a   Yeh, C Grace ^a  

^a CytoMed Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 METHOXY 4 [(PHENYLSULFONYLAMINO)CARBONYL]BENZYL] 1H INDAZOLE 6 CARBAMIC ACID CYCLOPENTYL ESTER; 2 [4 [2 (4 CHLOROPHENYLTHIO)ETHOXY] 5 (3 HYDROXY 3 METHYLUREIDOMETHYL) 3 METHOXYPHENYL] 5 (3,4,5 TRIMETHOXYPHENYL)TETRAHYDROFURAN; 3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 4 (5 METHOXY 3 METHYL 2 INDOLYL) 2,6 DIMETHYLPHENOL; 6 (2 CHLOROPHENYL) 9 [(3,4 DIMETHOXYPHENYL)THIOMETHYLTHIOCARBONYL] 4,7,8,10 TETRAHYDRO 1 METHYLPYRIDO[4',3':4,5]THIENO[3,2 F][1,2,4]TRIAZOLO[4,3 A][1,4]DIAZEPINE; APAFANT; ARACHIDONATE 5 LIPOXYGENASE; BENZOXAZINE DERIVATIVE; CMI 568; CP 93610; CP 95465; CP 96021; FURAN DERIVATIVE; LIPOXYGENASE INHIBITOR; PRANLUKAST; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG; ZILEUTON; [2 METHOXY 3 (N OCTADECYLCARBAMOYLOXY)PROPYL] (2 THIAZOLIOETHYL) PHOSPHATE;

ASTHMA; DRUG DESIGN; DRUG SYNTHESIS; INFLAMMATION; INJURY; NONHUMAN; PSORIASIS; REVIEW; RHEUMATOID ARTHRITIS; RHINITIS; SHOCK;

EID: 0029803516     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1996.021.09.381376     Document Type: Review

References (77)

1. Alabaster, V.A., Moore, B.A. New perspectives on basic mechanisms in lung disease. Drug intervention in asthma: Present and future. Thorax 1993, 48: 176-82.
2. (a) Peters, S.P. Mast cells and histamine in asthma. J Allergy Clin Immunol 1990, 86 (4, pt 2): 642-6.
3. (b) Piacentini, G.L., Kaliner, M.A. The potential roles of leukotrienes in bronchial asthma. Amer Rev Respir Dis 1991, 143 (5, pt 2): S96-9.
4. (c) Smith, L.J. The role of platelet-activating factor in asthma. Amer Rev Respir Dis 1991, 143 (5, pt 2): S100-2.
5. (a) Summers, J.B., Davidsen, S.K., Sheppard, G.S. Platelet-activating factor antagonists. Curr Pharm Des 1995, 1: 161-90.
6. (b) Summers, J.B., Albert, D.H. Platelet-activating factor antagonists. In: Advances in Pharmacology, Vol. 32. August, J.T., Anders, M.W., Murad, F., Coyle, J. (Eds.). Academic Press: New York 1995, 67-168.
7. (c) Hwang, S-B. Platelet-activating factor: Receptors and receptor antagonists. In: Lipid Mediators. Cunningham, F. (Ed.). Academic Press: London 1994, 297-360.
8. (a) Brooks, C.D.W., Summers, J.B. Modulator of leukotriene biosynthesis and receptor antagonist. J Med Chem 1995, 39: 2639-54.
9. (b) Ford-Hutchinson, A.W., Gresser, M., Young, R.N. 5-Lipoxygenase. Annu Rev Biochem 1994, 63: 383-417.
10. (c) Musser, J.H., Kreft, A.F. 5-Lipoxygenase: Properties, pharmacology, and the quinolinyl (bridged) aryl class of inhibitors. J Med Chem 1992, 35: 2501-24.
11. (d) Batt, D.G. 5-Lipoxyganase inhibitors and their anti-inflammatory activities. Prog Med Chem 1992, 29: 1-63.
12. (a) Blank, N.L., Snyder, F., Byer, LW., Brooks, B., Miurhead, E.E. Antihypertensive activity of an alkyl ether analog of phosphatidylcholine. Biochem Biophys Res Commun 1979, 90: 1194-200.
13. (b) Demopoulos, A., Pinckard, R.N., Hanahan, D.J. Platelet activating factor Evidence for 1-O-alkyl-2-acetyl-sn-glycerol-3-phosphocholine as the active component (a new class of lipid chemical mediators). J Biol Chem 1979, 254: 9355-8.
14. (c) Benveniste, J., Terence, M., Biadault, J., Boullet, C., Polonsky, J. Semisynthese et structure proposee du facteur actvant les plaquetts (PAF). PAF acether, un alkyl ether analog de la lyso-phosphatidylcholine. CR Acad Sci Paris [D289] 1979, 1037-40.
15. Terashita, Z-I., Tsushima, S., Yoshika, Y., Nomura, H., Inada, Y., Nishikawa, K. CV-3988 - A specific antagonist of platelet activating factor (PAF). Life Sci 1983, 32: 1975-82.
16. (a) Handley, D.A., Lee, M.L., Saunders, R.N. Evidence for a direct effect on vascular permeability of platelet activating factor induced hemoconcentration in the guinea pig. Thromb Haemost 1985, 54: 756-9.
17. (b) Robertson, D.N., Smith, G.M. CV-3988 inhibits in vivo platelet aggregation induced by PAF-acether and collagen. Eur J Pharmacol 1986, 123: 91-7.
18. (c) Arnout, J., Van Hecken, A., De Lepeleire, I. et al. Effectiveness and tolerability of CV-3988, a selective PAF antagonist, after intravenous administration to man. Brit J Clin Pharmacol 1988, 25: 445-51.
19. (a) E-5880. Drugs Fut 1992, 17: 1082-6.
20. (b) E-5880. Drugs Fut 1995, 20: 1276-7.
21. Sahoo, S.P., Graham, D.W., Acton, J. et al. Synthesis and biological activity of MK-287 (L-680,573): A potent, specific and orally active PAF receptor antagonist. Bioorg Med Chem Lett 1991, 1: 327-32.
22. (a) Weber, K.H., Heuer, H.O. Hetrazepines as antagonists of platelet activating factor. Med Res Rev 1989, 9: 181-218.
23. (b) Weber, K.H., Heuer, H. Structure-activity relationships and effects of platelet activating factor antagonists in the hetrazepine series. Int Arch Allergy Appl Immunol 1989, 88: 82-7.
24. (c) Casals-Stenzel, J. Thieno-triazolo-1,4-diazepines as antagonists of platelet-activating factor: Present status. Lipids 26: 1157-61.
25. Weber, K.H., Casals-Stenzel, H., Birke, F. et al. Influence of the 1,2-annelated heterocyclic ring on the PAF-antagonism of 1,4-diazepines. Clin Exp Pharmacol Physiol 1988, 13: (Suppl.): 3.
26. Takehara, S., Mikashima, H., Muramato, Y., Terasawa, M., Setoguchi, M., Tahara, T. Pharmacological actions of Y-24180, a new specific antagonist of platelet activating factor (PAF), II. Interactions with PAF and benzodiazepine receptors. Prostaglandins 1990, 40: 571-83.
27. Y-24180. IMSWord R&D Focus Online. London: IMSWord Publications, Ltd. January 3, 1994.
28. Davidsen, S.K., Summers, J.B., Albert, D.H. et al. N-(Acyloxyalkyl)pyridinum salts as soluble prodrugs of a potent platelet activating factor antagonist. J Med Chem 1994, 37: 4423-9.
29. (a) Parry, M.J., Alabaster, V.A., Cheeseman, H.E., Cooper, K., Rose, A., Keir, R.F. Pharmacological profile of UK-74,505, a novel and selective PAF antagonist with potent and prolonged activity. J Lipid Mediat Cell Signal 1994, 10: 251-68.
30. (b) Sanz, M.J., Weg, V.B., Walsh, D.T., Williams, T.J., Nourshargh, S. Differential effects of the PAF receptor antagonist UK-74,505 on neutrophil and eosinophil accumulation in guinea-pig skin. Brit J Pharmacol 1994, 113: 513-21.
31. (c) Pons, F., Rossi, A.G., Norman, K.E., Williams, T.J., Noursgargh, S. Role of platelet-activating factor (PAF) in platelet accumulation in rabbit skin: Effect of the novel long-acting PAF antagonist, UK-74505. Brit J Pharmacol 1993, 109: 234-42.
32. Fort F.L., Pratt, M.C., Carter, G.W. et al. Heinz bodies, methemoglobinemia, and hemolytic anemia induced in rats by 3-amino-1-(m-(trifluoromethyl)phenyl)-pyrazoline. Fund Appl Toxicol 1984, 4: 216-20.
33. Corey, E.J., Cashman, J.R., Kantner, S.S., Wright, S.W. Rationally designed, potent competitive inhibitors of leukotriene biosynthesis. J Amer Chem Soc 1984, 106: 1503-4.
34. Tateson, J.E., Randall, R.W., Reynolds, C.H. et al. Selective inhibition of arachidonate 5-lipoxygenase by novel acetohydroxamic acid: Biochemical assesment in vitro and ex vivo. Brit J Pharmacol 1988, 94: 528-39.
35. Summers, J.B., Gunn, B.P., Mazdiyasni, H. et al. In vivo characterization of hydroxamic acid inhibitor of 5-lipoxygenase. J Med Chem 1987, 30: 2121-6.
36. Riendeau, D., Falgueyret, J.P., Guay, J., Ueda, N., Yamamota, S. Pseudoperoxidase activity of 5-lipoxygenase stimulated by potent benzofuranol and N-hydroxyurea inhibitors of the lipoxygense reaction. Biochem J 1991, 274: 87-292.
37. (a) Summers, J.B., Gunn, B.P., Martin, J.G. et al. Structure-activity analysis of a class of orally active hydroxamic acid inhibitors of leukotriene biosynthesis. J Med Chem 1988, 31: 1960-4.
38. (b) Carter, G.W., Young, P.R., Albert, D.H. et al. 5-Lipoxygenase inhibitory activity of zileuton. J Pharmacol Exp Ther 1991, 256: 929-37.
39. (c) Jackson, W.P., Islip, P.J., Kneen, G., Pugh, A., Wales, P.J. Acetohydroxamic acids as potent selective orally active 5-lipoxygenase inhibitors. J Med Chem 1988, 31: 500-3.
40. Brooks, D.W., Carter, G.W. The discovery of zileuton (Leutrol). In: The Search for Antiinflammatory Drugs. Merluzzi, V.J., Adams, J. (Eds.). Birkhauser: Boston 1995, 129-60.
41. (a) Bell, L.R., Bouska, J.F., Malo, P.E. et al. Optimization of the potency and duration of action of N-hydroxyurea 5-lipoxygenase inhibitors. J Pharmacol Exp Ther 1995, 272: 724-31.
42. (b) Basha, A., Ratajczyk, J.D., Stewart, A.O., Bell, R.L., Carter, G.W., Brooks, C.D.W. SAR on acetylenic N-hydroxy ureas: Discovery of ABT-761. 209th ACS Meet (April 2-6, Anaheim) 1995, MEDI 184.
43. (c) Brooks, C.D.W., Stewart, A.O., Basha, A. et al. (R)-(+)-N-[3-[5-[(4-Fluorophenyl)methyl]-2-thienyl]-1-methyl-2-propynyl]-N- hydroxyurea (ABT761), a second-generation 5-lipoxygenase inhibitor. J Med Chem 1995, 38: 4768-75.
44. Crawley, G.C., Foster, S.J., McMillan, R.M., Walker, E.R.H. Discovery of ZD2138, a potent selective, well tolerated, nonredox inhibitor of the enzyme 5-lipoxygenase. In: The Search for Antiinflammatory Drugs. Merluzzi, V.J., Adams, J. (Eds.). Birkhauser: Boston 1995, 190-231.
45. Bird, T.G.C., Bruneau, P., Crawley, G.C. et al. (Methoxyalkyl)thiazoles: A new series of potent, selective, and orally active 5-lipoxygenase inhibitors displaying high enantioselectivity. J Med Chem 1991, 34: 2176-86.
46. (a) Nasser, S.M., Bell, G.S., Foster, S.J. et al. Effect of the 5-lipoxygenase inhibitor ZD2138 on aspirin-induced asthma. Thorax 1994, 49: 749-56.
47. (b) Nasser, S.M., Bell, G.S., Spruce, K. et al. Effect of the 5-lipoxygenase inhibitor ZD2138 on allergen-induced early and late asthmatic responses. Thorax 1994, 49: 743-8.
48. Rouzer, C.A., Kargman, S. Translocation of 5-lipoxygenase to the membrane in human leukocytes challenged with ionophore A23187. J Biol Chem 1988, 263: 10980-8.
49. Rouzer, C.A., Ford-Hutchinson, A.W., Morton, H.E., Gillard, J.W. MK-886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore challenged leukocytes. J Biol Chem 1990, 265: 1436-42.
50. Bel, E.H., Tanaka, W., Spector, R. et al. MK-886, an effective oral leukotriene biosynthesis inhibitor on antigen-induced early and late asmthatic reactions in man. Amer Rev Respir Dis 1990, 141: A31.
51. Woods, K.W., Brooks, C.D.W., Maki, R.G. et al. Discovery of the leukotriene biosynthesis inhibitor A-81834. 209th ACS Meet (April 2-6, Anaheim) 1995, MEDI 183.
52. (a) Lewis, R.A., Austen, K.F., Soberman, R.J. Leukotrienes and other products of the 5-lipoxygenase pathway. New Engl J Med 1990, 323: 645-55.
53. (b) Henderson, W.R. The role of leukotrienes in inflammation. Ann Intern Med 1994, 121: 684-97.
54. Orange, R.P., Austen, K.F. Slow reacting substance of anaphylaxis. Adv Immunol 1969, 10: 105-44.
55. 4. Tetrahedron Lett 1988, 29: 143-6.
56. (a) Hay, D.W.P., Griswold, D.E. Inhibitors of fatty acid-derived mediators. In: Lipid Mediators. Cunningham, F. (Ed.). Academic Press: London 1994, 117-79 and references therein.
57. Inflammation Research Association Meeting Summary. New York Academy of Sciences, May 19, 1994.
58. Hay, D.W.P., Torphy, R.J., Undem, B.J. Cysteinyl leukotrienes in asthma: Old mediators up to new tricks. Trends Pharmacol Sci 1995, 16: 304-9.
59. Augstein, J., Farmer, J.B., Lee, T.B., Sheard, P., Tattersall, M.L. Selective inhibition of slow reacting substance of anaphylaxis. Nature (New Biol) 1973, 245: 215-6.
60. Sheard, P., Lee, T.B., Tattersal, M.L.K. Further studies of the SRS-A antagonist FPL55712. Monogr Allergy 1977, 12: 245-9.
61. (a) Brown, F.J. Discovery of Accolate (ICI 204,219), a peptide leukotriene antagonist for asthma. In: The Search for Antiinflammatory Drugs. Merluzzi, V.J., Adams, J. (Eds.). Birkhauser: Boston 1995, 161-89.
62. (b) New Product Intros. Drug News Perspect 1996, 9: 359-60.
63. (c) Zeneca asthma drug, first of a new class, gets FDA approval. CytoMed, Inc. News Release 1996, September 27.
64. O'Donnell, M., Welton, A. Comparison of the pulmonary pharmacology of leukotrienes and PAF: Effects of their antagonists. In: Therapeutic Approaches to Inflammatory Diseases. Lewis. A.J., Doherty, N.S., Ackerman, N.R. (Eds.). Elsevier: New York 1989, 147-93.
65. Yoshikawa, D., Goto, F. Effect of platelet-activating factor antagonist and leukotriene antagonist on endotoxin shock in the rat: Role of the leukocyte. Circ Shock 1992, 38: 29-33.
66. (a) Fernandez-Gallardo, S., Gijon, M.A., Garcia, C., Furio, V., Liu, F.T., Crespo, M.S. The role of platelet-activating factor and peptidoleukotrienes in the vascular changes of rat passive anaphylaxis. Brit J Pharmacol 1992, 105: 119-25.
67. (b) 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. Plenum Publishers: New York 1987, 153-90.
68. Shen, T.Y. Chemical and biochemical characterization of lignan analogs as novel PAF receptor antagonists. Lipids 1991, 26: 1154-6.
69. Goldstein, D.M., Shen, T.Y. Dual inhibitors of platelet-activating factor and 5-lipoxygenase. 2,4-Diaryl-1,3-dithiolanes. Med Chem Res 1992, 2: 443-50, 451-6.
70. (a) Cai, X., Hussoin, M.S., Killian, D.B. et al. Synthesis of substituted-hydroxyureidyl diaryltetrahydrofurans, a potent class of dual inhibitors of 5-lipoxygenase (5-LO) and platelet-activating factor (PAF). 207th ACS Meet (March 13-17, San Diego) 1994, MEDI 123.
71. (b) Hussoin, M.S., Cai, X., Scannell, R. et al. Platelet-activating factor and 5-lipoxygenase inhibitory activity of (CMI-206) hydroxyureidyl tetrahydrofuran/tetrahydrothiophene. 208th ACS Meet (Aug 21-25, Washington, DC) 1994, MEDI 126.
72. (c) Hussoin, M.S., Cai, X., Scannell, R. et al. CMI-206.A potent dual platelet activating factor antagonist and 5-lipoxygenase inhibitor. Bioorg Med Chem Lett 1995, 5: 643-8.
73. (d) Hussoin, M.S., Biftu, T., Cai, X. et al. Synthesis and structure activity of a potent dual-acting platelet activating factor and 5-lipoxygenase inhibitor. 211th ACS Meet (March 24-28, New Orleans) 1996, MEDI 205.
74. Yeh, C.G., Eckman, J., Cai, X., Ip, S.H. A dual-acting inhibitor of 5-lipoxygenase and platelet-activating factor, CMI-392, reduces inflammation in mouse ear edema models. J Invest Dermatol 1995, 104: 649.
75. Demonchaux, P., Lenoir, P., Augert, G., Dupassieux, P. Design of pyrrolo-1,4-benzoxazine derivatives as inhibitors of 5-lipoxygenase and PAF antagonists with antihistaminic properties. Bioorg Med Chem Lett 1994, 4: 2383-8.
76. Paris, D., Cottin, M., Demonchaux, P. et al. Synthesis, structure-activity relationships, and pharmacological evaluation of pyrrolo[3,2,1-ij]quinoline derivatives: Potent histamine and platelet-activating factor antagonism and 5-lipoxygenase inhibitory properties. Potential therapeutic application in asthma. J Med Chem 1995, 38: 669-85.
77. 4)/platelet activating factor antagonists CP-96,021 and CP-96,486. 7th Int Conf Inflamm Res Assoc (Sept 25-29, White Haven) 1994.