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Volumn 37, Issue 7, 1994, Pages 913-923

Benzoxazolamines and Benzothiazolamines: Potent, Enantioselective Inhibitors of Leukotriene Biosynthesis with a Novel Mechanism of Action

Author keywords

[No Author keywords available]

Indexed keywords

3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 6 [[3 FLUORO 5 (3,4,5,6 TETRAHYDRO 4 METHOXY 2H PYRAN 4 YL)]PHENOXYMETHYL] 1 METHYL 2 QUINOLONE; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONIC ACID; CALCIMYCIN; ENOFELAST; ENZYME INHIBITOR; LEUKOTRIENE; LEUKOTRIENE B4; LEUKOTRIENE C4; LEUKOTRIENE D4; N (2 BENZOTHIAZOLYL)PHENYLALANINE ETHYL ESTER; N [2 CYCLOHEXYL 1 (2 PYRIDINYL)ETHYL] 5 METHYL 2 BENZOXAZOLAMINE; PHOSPHOLIPASE A2; UNCLASSIFIED DRUG; ZILEUTON;

EID: 0028194945     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00033a008     Document Type: Article
Times cited : (29)

References (32)
  • 1
    • 0024435580 scopus 로고
    • Biochemistry of the Lipoxygenase Pathways in Neutrophils
    • Borgeat, P. Biochemistry of the Lipoxygenase Pathways in Neutrophils. Can. J. Physiol. Pharmacol. 1989, 67, 936-942.
    • (1989) Can. J. Physiol. Pharmacol. , vol.67 , pp. 936-942
    • Borgeat, P.1
  • 2
    • 0024368596 scopus 로고
    • Enzymes Involved in the Biosynthesis of Leukotriene B4
    • Samuelsson, B.; Funk, C. D. Enzymes Involved in the Biosynthesis of Leukotriene B4. J. Biol. Chem. 1989, 264, 19469-19472.
    • (1989) J. Biol. Chem. , vol.264 , pp. 19469-19472
    • Samuelsson, B.1    Funk, C.D.2
  • 3
    • 0026736070 scopus 로고
    • 5-Lipoxygenase: Properties, Pharmacology, and the Quinolinyl (bridged) aryl Class of Inhibitors
    • Musser, J. H.; Kreft, A. F. 5-Lipoxygenase: Properties, Pharmacology, and the Quinolinyl (bridged) aryl Class of Inhibitors. J. Med. Chem. 1992, 35, 2501-2513.
    • (1992) J. Med. Chem. , vol.35 , pp. 2501-2513
    • Musser, J.H.1    Kreft, A.F.2
  • 4
    • 0025647649 scopus 로고
    • Inhibitors of Leukotriene Biosynthesis
    • Summers, J. B. Inhibitors of Leukotriene Biosynthesis. Drug News Perspect. 1990, 3, 3517-3526.
    • (1990) Drug News Perspect. , vol.3 , pp. 3517-3526
    • Summers, J.B.1
  • 5
    • 0025815488 scopus 로고
    • Peptide Leukotrienes: Current Statue of Research
    • Shaw, A.; Krell, R. D. Peptide Leukotrienes: Current Statue of Research. J. Med. Chem. 1991, 34, 1235-1242.
    • (1991) J. Med. Chem. , vol.34 , pp. 1235-1242
    • Shaw, A.1    Krell, R.D.2
  • 7
    • 0019254822 scopus 로고
    • Leukotrienes are Potent Constrictors of Human Bronchi
    • (London)
    • Dahlen, S.-E.; Hedquist, P.; Hammerstrom, B.; Samuelsson, B. Leukotrienes are Potent Constrictors of Human Bronchi. Nature (London) 1980, 288, 484-486.
    • (1980) Nature , vol.288 , pp. 484-486
    • Dahlen, S.-E.1    Hedquist, P.2    Hammerstrom, B.3    Samuelsson, B.4
  • 8
    • 0021269295 scopus 로고
    • Comparative Effects of Inhaled Leukotriene C4, Leukotriene D4 and Histamine in Normal Human Subjects
    • Barnes, N. C.; Piper, P. J.; Costello, J. F. Comparative Effects of Inhaled Leukotriene C4, Leukotriene D4 and Histamine in Normal Human Subjects. Thorax 1984, 39, 500-504.
    • (1984) Thorax , vol.39 , pp. 500-504
    • Barnes, N.C.1    Piper, P.J.2    Costello, J.F.3
  • 9
    • 0019971503 scopus 로고
    • Slow Reacting Substances LTC4 and LTD4 Increase the Release of Mucus from Human Airways In Vitro
    • Marom, Z.; Shelhamer, J. H.; Bach, M. K.; Morton, D. R.; Kaliner, M. Slow Reacting Substances LTC4 and LTD4 Increase the Release of Mucus from Human Airways In Vitro. Am. Rev. Respir. Dis. 1982, 126, 449-451.
    • (1982) Am. Rev. Respir. Dis. , vol.126 , pp. 449-451
    • Marom, Z.1    Shelhamer, J.H.2    Bach, M.K.3    Morton, D.R.4    Kaliner, M.5
  • 10
    • 85022407458 scopus 로고
    • Effect of Inhaled Leukotriene (LT) D4 on Airway Hyperreactivity in Normal Subjects: Comparison with Histamine and Platelet Activating Factor (PAF)
    • Kaye, M. G.; Smith, L. J. Effect of Inhaled Leukotriene (LT) D4 on Airway Hyperreactivity in Normal Subjects: Comparison with Histamine and Platelet Activating Factor (PAF). Clin. Res. 1989, 37, 478A.
    • (1989) Clin. Res. , vol.37 , pp. 478A
    • Kaye, M.G.1    Smith, L.J.2
  • 11
    • 0025925113 scopus 로고
    • Leukotrienes C4, D4, and E4 Enhance Histamine Responsiveness in Asthmatic Airways
    • Arm, J. P.; Spur, B. W.; Lee, T. H. Leukotrienes C4, D4, and E4 Enhance Histamine Responsiveness in Asthmatic Airways. Am. Rev. Resp. Dis. 1991, 144, 1053-1057.
    • (1991) Am. Rev. Resp. Dis. , vol.144 , pp. 1053-1057
    • Arm, J.P.1    Spur, B.W.2    Lee, T.H.3
  • 12
    • 0025164256 scopus 로고
    • Leukotrienes and Other Products of the 5-Lipoxygenase Pathway. Biochemistry and Relation to Pathobiology in Human Diseases
    • Lewis, R. A.; Austen, K. F.; Soberman, R. J. Leukotrienes and Other Products of the 5-Lipoxygenase Pathway. Biochemistry and Relation to Pathobiology in Human Diseases. N. Engl. J. Med. 1990, 323, 645-654.
    • (1990) N. Engl. J. Med. , vol.323 , pp. 645-654
    • Lewis, R.A.1    Austen, K.F.2    Soberman, R.J.3
  • 13
    • 0025129159 scopus 로고
    • 5-Lipoxygenase: A Rational Target for Therapy of Inflammatory Bowel Diseases?
    • Wallace, J. L. 5-Lipoxygenase: A Rational Target for Therapy of Inflammatory Bowel Diseases? Trends Pharmacol. Sci. 1990, 11, 51-53.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 51-53
    • Wallace, J.L.1
  • 15
    • 1642341278 scopus 로고
    • Double-Blind Multicenter Study of Zileuton, a Potent 5-Lipoxygenase (5-LO) Inhibitor Versus Placebo in the Treatment of Spontaneous Asthma in Adults
    • Israel, E.; Drazen, J. M.; Perlman, H.; Cohn, J.; Rubin, P. A. Double-Blind Multicenter Study of Zileuton, a Potent 5-Lipoxygenase (5-LO) Inhibitor Versus Placebo in the Treatment of Spontaneous Asthma in Adults. J. Allergy Clin. Immunol. 1992,89, 236.
    • (1992) J. Allergy Clin. Immunol. , vol.89 , pp. 236
    • Israel, E.1    Drazen, J.M.2    Perlman, H.3    Cohn, J.4    Rubin, P.A.5
  • 16
    • 0025802839 scopus 로고
    • Lung Function Improvement in Asthma with a Cysteinyl-Leukotriene Reception Antagonist
    • Hui, K. P.; Barnes, N. C. Lung Function Improvement in Asthma with a Cysteinyl-Leukotriene Reception Antagonist. Lancet 1991, 337, 1062-1063.
    • (1991) Lancet , vol.337 , pp. 1062-1063
    • Hui, K.P.1    Barnes, N.C.2
  • 17
    • 0025873761 scopus 로고
    • 2,6-Disubstituted-4-(2-arylethenyl) phenol 5-Lipoxygenase Inhibitors: Development and Profile of BI-L-239
    • Lazer E. S.; Farina, P. R.; Gundel, R. H.; Wegner, C. D. 2,6-Disubstituted-4-(2-arylethenyl) phenol 5-Lipoxygenase Inhibitors: Development and Profile of BI-L-239. Drugs Future 1991, 16, 641-646.
    • (1991) Drugs Future , vol.16 , pp. 641-646
    • Lazer, E.S.1    Farina, P.R.2    Gundel, R.H.3    Wegner, C.D.4
  • 18
    • 0025979255 scopus 로고
    • Pseudoperoxidase activity of 5-Lipoxygenase Stimulated by Potent Benzofuranol and N-Hydroxyurea Inhibitors of the Lipoxygenase Reaction
    • Reindeau, D.; Falgueyret, J.-P.; Guay, J.; Veda, N.; Yamamoto, S. Pseudoperoxidase activity of 5-Lipoxygenase Stimulated by Potent Benzofuranol and N-Hydroxyurea Inhibitors of the Lipoxygenase Reaction. Biochem J. 1991, 274, 287-292.
    • (1991) Biochem J. , vol.274 , pp. 287-292
    • Reindeau, D.1    Falgueyret, J.-P.2    Guay, J.3    Veda, N.4    Yamamoto, S.5
  • 20
    • 0025098441 scopus 로고
    • MK886, a Potent and Specific Leukotriene Biosynthesis Inhibitor Blocks and Reverses the Membrane Association of 5-Lipoxygenase in Ionophore-challenged Leukocytes
    • Rouzer, C. A.; Ford-Hutchinson, A. W.; Morton, M. E.; Gillard, J. W. MK886, a Potent and Specific Leukotriene Biosynthesis Inhibitor Blocks and Reverses the Membrane Association of 5-Lipoxygenase in Ionophore-challenged Leukocytes. J. Biol. Chem. 1990, 265,1436-1442.
    • (1990) J. Biol. Chem. , vol.265 , pp. 1436-1442
    • Rouzer, C.A.1    Ford-Hutchinson, A.W.2    Morton, M.E.3    Gillard, J.W.4
  • 22
    • 0025156687 scopus 로고
    • The Role of Eicosanoids in Allergen-Induced Early and Late Bronchial Responses in Allergic Sheep
    • Thromboxane, Leukotriene Res.
    • Abraham, W. M. The Role of Eicosanoids in Allergen-Induced Early and Late Bronchial Responses in Allergic Sheep. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1990, 201-208.
    • (1990) Adv. Prostaglandin , pp. 201-208
    • Abraham, W.M.1
  • 23
    • 0010365024 scopus 로고
    • Benzoxazole Derivatives. I. 2-Mercaptobenzoxazoles
    • Katz, L.; Cohen, M. S. Benzoxazole Derivatives. I. 2-Mercaptobenzoxazoles. J. Org. Chem. 1954, 19, 758-766.
    • (1954) J. Org. Chem. , vol.19 , pp. 758-766
    • Katz, L.1    Cohen, M.S.2
  • 24
    • 33544455685 scopus 로고
    • The Resolution of Racemic Amines by the Formation of Diastereomeric Amides with Amino Acids
    • Miao, C. K.; Sorcek, R.; Nagel, J. H. The Resolution of Racemic Amines by the Formation of Diastereomeric Amides with Amino Acids. Org. Prep. Proced. Int. 1992, 24, 87-91.
    • (1992) Org. Prep. Proced. Int. , vol.24 , pp. 87-91
    • Miao, C.K.1    Sorcek, R.2    Nagel, J.H.3
  • 25
    • 0025294913 scopus 로고
    • Effect of Structure on Potency and Selectivity in 2,6-Disubstituted 4-(2-arylethenyl)phenol Lipoxygenase Inhibitors
    • Lazer, E. S.; Wong, H.-C.; Wegner, C. D.; Graham, A. G.; Farina, P. R. Effect of Structure on Potency and Selectivity in 2,6-Disubstituted 4-(2-arylethenyl)phenol Lipoxygenase Inhibitors. J. Med. Chem. 1990, 33, 1892-1898.
    • (1990) J. Med. Chem. , vol.33 , pp. 1892-1898
    • Lazer, E.S.1    Wong, H.-C.2    Wegner, C.D.3    Graham, A.G.4    Farina, P.R.5
  • 27
    • 0019592046 scopus 로고
    • Pharmacokinetic and Pharmacodynamic Modeling In Vivo
    • Holford, N. H. G.; Sheiner, L. B. Pharmacokinetic and Pharmacodynamic Modeling In Vivo. Crit. Rev. Bioeng. 1981, 5, 273-322.
    • (1981) Crit. Rev. Bioeng. , vol.5 , pp. 273-322
    • Holford, N.H.G.1    Sheiner, L.B.2
  • 28
    • 0020315441 scopus 로고
    • Kinetics of Pharmacologic Response
    • Holford, N. H. G.; Sheiner, L. B. Kinetics of Pharmacologic Response. Pharmacol. Ther. 1982, 16, 143-166.
    • (1982) Pharmacol. Ther. , vol.16 , pp. 143-166
    • Holford, N.H.G.1    Sheiner, L.B.2
  • 29
    • 0041673762 scopus 로고
    • Some Heterocyclic Aldehyde Thiosemicarbazones Possessing Anti-Viral Activity
    • Campaigne, E.; Thompson, R. L.; Van Werth, J. E. Some Heterocyclic Aldehyde Thiosemicarbazones Possessing Anti-Viral Activity. J. Med. Chem. 1959, 1, 577-599.
    • (1959) J. Med. Chem. , vol.1 , pp. 577-599
    • Campaigne, E.1    Thompson, R.L.2    Van Werth, J.E.3
  • 30
    • 33947455162 scopus 로고
    • The Reaction of Nitriles with Hydrazoic Acid: Synthesis of Monosubstituted Tetrazoles
    • Mihina, J. S.; Herbst, R. M. The Reaction of Nitriles with Hydrazoic Acid: Synthesis of Monosubstituted Tetrazoles. J. Org. Chem. 1950, 15, 1082-1092.
    • (1950) J. Org. Chem. , vol.15 , pp. 1082-1092
    • Mihina, J.S.1    Herbst, R.M.2
  • 31
    • 0001642794 scopus 로고
    • Preparation of Methyl Ketones by the Sequential Treatment of Carboxylic Acids with Methyllithium and Chlorotrimethylsilane
    • Rubottom, G. M.; Kim, C. Preparation of Methyl Ketones by the Sequential Treatment of Carboxylic Acids with Methyllithium and Chlorotrimethylsilane. J. Org. Chem. 1983, 48, 1550-1552.
    • (1983) J. Org. Chem. , vol.48 , pp. 1550-1552
    • Rubottom, G.M.1    Kim, C.2
  • 32
    • 0018073126 scopus 로고
    • Intracellular Control of Human Neutrophil Secretion. I. C5a-Induced Stimulus-Specific Desensitization and the Effects of Cytochalasin B
    • Henson, P. M.; Zanolari, B.; Schwartzman, N. A.; Hong, S. R. Intracellular Control of Human Neutrophil Secretion. I. C5a-Induced Stimulus-Specific Desensitization and the Effects of Cytochalasin B. J. Immunol. 1978,121, 861-855.
    • (1978) J. Immunol. , vol.121 , pp. 855-861
    • Henson, P.M.1    Zanolari, B.2    Schwartzman, N.A.3    Hong, S.R.4


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