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Volumn 38, Issue 9, 1995, Pages 1473-1481

Synthesis and Antiinflammatory Activity of Certain 5,6,7,8-Tetrahydroquinolines and Related Compounds

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 1 (3 TRIFLUOROMETHYLPHENYL) 2 PYRAZOLINE; 5,6,7,8 TETRAHYDROQUINOLINE DERIVATIVE; 6,7,8,9 TETRAHYDRO 3 METHYL ALPHA (4 METHYLPHENYL) 5H CYCLOHEPTA[B]PYRIDINE 2 METHANOL; 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[B]PYRIDINE DERIVATIVE; ANTIULCER AGENT; ARACHIDONATE 5 LIPOXYGENASE; BENZYLIDENE DERIVATIVE; CL 1004; IBUPROFEN; LIPOXYGENASE INHIBITOR; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; WY 28342; ZILEUTON;

EID: 0028946299     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00009a008     Document Type: Article
Times cited : (38)

References (42)
  • 2
    • 0025856636 scopus 로고
    • Nonsteroidal Antiinflammatory Drugs- Differences and Similarities
    • Brooks, P. M.; Day, R. O. Nonsteroidal Antiinflammatory Drugs- Differences and Similarities. N. Engl. J. Med. 1991, 324, 1716-1725.
    • (1991) N. Engl. J. Med. , vol.324 , pp. 1716-1725
    • Brooks, P.M.1    Day, R.O.2
  • 4
    • 0026443983 scopus 로고
    • NSAID, Ulcers and Prostaglandins
    • Kimmey, M. B. NSAID, Ulcers and Prostaglandins. J. Rheumatol. 1992, 19 (Suppl. 36), 67-73.
    • (1992) J. Rheumatol. , vol.19 , pp. 67-73
    • Kimmey, M.B.1
  • 5
    • 0024591782 scopus 로고
    • Mechanisms of Nonsteroidal AntiInflammatory Drug-Induced Gastric Damage
    • Schoen, R. T.; Vender, R. J. Mechanisms of Nonsteroidal AntiInflammatory Drug-Induced Gastric Damage. Am. J. Med. 1989, 86, 449-458.
    • (1989) Am. J. Med. , vol.86 , pp. 449-458
    • Schoen, R.T.1    Vender, R.J.2
  • 6
    • 0026653597 scopus 로고
    • Effect of Nonsteroidal Anti-inflammatory Drugs on Endogenous Gastrointestinal Prostaglandins and Therapeutic Strategies for Prevention and Treatment of Nonsteroidal Anti-inflammatory Drug-Induced Damage
    • Cryer, B.; Feldmann, M. Effect of Nonsteroidal Anti-inflammatory Drugs on Endogenous Gastrointestinal Prostaglandins and Therapeutic Strategies for Prevention and Treatment of Nonsteroidal Anti-inflammatory Drug-Induced Damage. Arch. Intern. Med. 1992, 152 (6), 1145-1155.
    • (1992) Arch. Intern. Med. , vol.152 , Issue.6 , pp. 1145-1155
    • Cryer, B.1    Feldmann, M.2
  • 7
    • 0023696547 scopus 로고
    • The Role of Leukotrienes in the Pathogenesis of Gastric Ulceration
    • Boughton-Smith, N. K.; Whittle, B. J. R. The Role of Leukotrienes in the Pathogenesis of Gastric Ulceration. Pharm. Res. Commun. 1988, 20, 919-934.
    • (1988) Pharm. Res. Commun. , vol.20 , pp. 919-934
    • Boughton-Smith, N.K.1    Whittle, B.J.R.2
  • 8
    • 0026742483 scopus 로고
    • Indomethacin- induced leukocyte adhesion in mesenteric venules: Role of lipoxygenase products
    • Asako, H.; Kubes, P.; Wallace, J. Gaginella, T.; Wolf, R. E.; Granger, N. Indomethacin- induced leukocyte adhesion in mesenteric venules: Role of lipoxygenase products. Am. J. Physiol. 1992, 262 (5), G903-8.
    • (1992) Am. J. Physiol. , vol.262 , Issue.5 , pp. G903-G908
    • Asako, H.1    Kubes, P.2    Wallace, J.3    Gaginella, T.4    Wolf, R.E.5    Granger, N.6
  • 9
    • 0024370199 scopus 로고
    • Eicosanoids and Rheumatology: Inflammatory and Vascular Aspects
    • Belch, J. J. F. Eicosanoids and Rheumatology: Inflammatory and Vascular Aspects. Prostaglandins, Leukotrienes Essent. Fatty Acids 1989, 36, 219-234.
    • (1989) Prostaglandins, Leukotrienes Essent. Fatty Acids , vol.36 , pp. 219-234
    • Belch, J.J.F.1
  • 11
    • 77956816035 scopus 로고
    • Modulation of Arachidonic Acid Metabolism in the Treatment of Rheumatoid Arthritis
    • Allen, R. C., Ed.; Academic Press: New York
    • Carty, T. J.; Marfat, A.; Masamune, H. Modulation of Arachidonic Acid Metabolism in the Treatment of Rheumatoid Arthritis. In Annual Reports in Medicinal Chemistry, Allen, R. C., Ed.; Academic Press: New York, 1988; Vol. 23, pp 181-189.
    • (1988) Annual Reports in Medicinal Chemistry , vol.23 , pp. 181-189
    • Carty, T.J.1    Marfat, A.2    Masamune, H.3
  • 12
    • 0028289770 scopus 로고
    • (6, 7- Diaryldihydropyrrolizin-5-yl) acetic Acids, a Novel Class of Potent Dual Inhibitors of Both Cyclooxygenase and 5-Lipoxygenase
    • Laufer, S. A.; Augustin, J.; Dannhardt, G.; Kiefer, W. (6, 7- Diaryldihydropyrrolizin-5-yl) acetic Acids, a Novel Class of Potent Dual Inhibitors of Both Cyclooxygenase and 5-Lipoxygenase. J. Med. Chem. 1994, 37, 1894-1897.
    • (1994) J. Med. Chem. , vol.37 , pp. 1894-1897
    • Laufer, S.A.1    Augustin, J.2    Dannhardt, G.3    Kiefer, W.4
  • 13
    • 0027301137 scopus 로고
    • 1, 3, 4-Oxadiazole, 1, 3, 4-Thiadiazole, and 1, 2, 4- Triazole Analogs of the Fenamates; In Vitro Inhibition of Cyclooxygenase and 5-Lipoxygenase Activities
    • Boschelli, D. H.; Connor, D. T.; Bornemeier, D. A.; Dyer, R. D.; Kennedy, J. A.; Kuipers, P. J.; Okonkwo, G. C.; Schrier, D. J.; Wright, C. D. 1, 3, 4-Oxadiazole, 1, 3, 4-Thiadiazole, and 1, 2, 4- Triazole Analogs of the Fenamates; In Vitro Inhibition of Cyclooxygenase and 5-Lipoxygenase Activities. J. Med. Chem. 1993, 36, 1802-1810.
    • (1993) J. Med. Chem. , vol.36 , pp. 1802-1810
    • Boschelli, D.H.1    Connor, D.T.2    Bornemeier, D.A.3    Dyer, R.D.4    Kennedy, J.A.5    Kuipers, P.J.6    Okonkwo, G.C.7    Schrier, D.J.8    Wright, C.D.9
  • 14
    • 0026730087 scopus 로고
    • Novel 1, 2, 4-Oxadioazoles and 1, 2, 4-Thiadiazoles as Dual 2- Lipoxygenase and Cyclooxygenase Inhibitors
    • Unangst, P. C.; Shrum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. Novel 1, 2, 4-Oxadioazoles and 1, 2, 4-Thiadiazoles as Dual 2- Lipoxygenase and Cyclooxygenase Inhibitors. J. Med. Chem. 1992, 35, 3691-3698.
    • (1992) J. Med. Chem. , vol.35 , pp. 3691-3698
    • Unangst, P.C.1    Shrum, G.P.2    Connor, D.T.3    Dyer, R.D.4    Schrier, D.J.5
  • 16
    • 0028031723 scopus 로고
    • Synthesis and Biological Evaluation of 5[[3, 5-Bis (1, 1- dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel Dual 5-Lipoxygenase and Cyclooxygenase Inhibitors with Antiinflammatory Activity
    • Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, D. C.; Schrier, D. J.; Dyer, R. D. Synthesis and Biological Evaluation of 5[[3, 5-Bis (1, 1- dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel Dual 5-Lipoxygenase and Cyclooxygenase Inhibitors with Antiinflammatory Activity. J. Med. Chem. 1994, 37, 322-328.
    • (1994) J. Med. Chem. , vol.37 , pp. 322-328
    • Unangst, P.C.1    Connor, D.T.2    Cetenko, W.A.3    Sorenson, R.J.4    Kostlan, C.R.5    Sircar, J.C.6    Wright, D.C.7    Schrier, D.J.8    Dyer, R.D.9
  • 17
    • 85022455207 scopus 로고
    • G. B. Patent 2, 138, 812A
    • John Wyeth & Brother Ltd., G. B. Patent 2, 138, 812A, 1986.
    • (1986)
  • 18
    • 0020622463 scopus 로고
    • Synthesis and Gastric Antisecretory Properties of 4, 5-Unsaturated Derivatives of 15-Deoxy-16-hydroxy-16-methylprostaglandin Ei
    • Collins, P. W.; Dajani, E. Z.; Pappo, R.; Gasiecki, A. F.; Bianchi, R. G.; Woods, E. M. Synthesis and Gastric Antisecretory Properties of 4, 5-Unsaturated Derivatives of 15-Deoxy-16-hydroxy-16-methylprostaglandin Ei. J. Med. Chem. 1983, 26, 786-790.
    • (1983) J. Med. Chem. , vol.26 , pp. 786-790
    • Collins, P.W.1    Dajani, E.Z.2    Pappo, R.3    Gasiecki, A.F.4    Bianchi, R.G.5    Woods, E.M.6
  • 19
    • 0015003818 scopus 로고
    • Prevention of duodenal ulcers by administration of prostaglandin E2 (PGE2)
    • Robert, A.; Stowe, D. F.; Nezamis, J. E. Prevention of duodenal ulcers by administration of prostaglandin E2 (PGE2). Scand. J. Gastroenterol. 1971, 6, 303-305.
    • (1971) Scand. J. Gastroenterol. , vol.6 , pp. 303-305
    • Robert, A.1    Stowe, D.F.2    Nezamis, J.E.3
  • 20
    • 85022552680 scopus 로고
    • 8th ed.; Gilman, A. G., Goodman, L. S., Rail, T. W., Nies, S. N., Taylor, P., Eds.; Pergamon Press: New York
    • The Pharmacological Basis of Therapeutics, 8th ed.; Gilman, A. G., Goodman, L. S., Rail, T. W., Nies, S. N., Taylor, P., Eds.; Pergamon Press: New York, 1990; pp 642 and 911.
    • (1990) The Pharmacological Basis of Therapeutics , pp. 642-911
  • 21
    • 33845471512 scopus 로고
    • Polyaza Cavity-Shaped Molecules. Annelated Derivatives of 2-(2′-Pyridyl)-1, 8-naphthyridine and 2, 2′-Bi-1, 8-naphthyridine
    • Thummel, R. P.; Lefoulon, F.; Cantu, D.; Mahadevan, R. Polyaza Cavity-Shaped Molecules. Annelated Derivatives of 2-(2′-Pyridyl)-1, 8-naphthyridine and 2, 2′-Bi-1, 8-naphthyridine. J. Org. Chem. 1984, 49, 2208-2212.
    • (1984) J. Org. Chem. , vol.49 , pp. 2208-2212
    • Thummel, R.P.1    Lefoulon, F.2    Cantu, D.3    Mahadevan, R.4
  • 22
    • 13844249973 scopus 로고
    • Synthesis, Metal Complex Formation, and Resolution of a New C2 Diazabiaryl Ligand: Cyclo-octa[2, l-b: 3, 4-b′]dipyridine
    • Wang, X. C.; Cui, Y. X.; Mak, T. C. W.; Wong, H. N. C. Synthesis, Metal Complex Formation, and Resolution of a New C2 Diazabiaryl Ligand: Cyclo-octa[2, l-b: 3, 4-b′]dipyridine. J. Chem. Soc., Chem. Commun. 1990, 167-169.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 167-169
    • Wang, X.C.1    Cui, Y.X.2    Mak, T.C.W.3    Wong, H.N.C.4
  • 23
    • 85083263815 scopus 로고
    • The Peterson Reaction
    • Ager, D. J. The Peterson Reaction. Synthesis 1984, 384-398.
    • (1984) Synthesis , pp. 384-398
    • Ager, D.J.1
  • 24
    • 2142664284 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. Part II. Preparation and Reactions of Substituted 5, 6, 7, 8- Tetrahydroquinoline-8-carboxlic Esters
    • Crossley, R.; Curran, A. C. W.; Hill, D. G. 5, 6, 7, 8-Tetrahydroquinolines. Part II. Preparation and Reactions of Substituted 5, 6, 7, 8- Tetrahydroquinoline-8-carboxlic Esters. J. Chem. Soc., Perkin Trans. I 1976, 977-982.
    • (1976) J. Chem. Soc., Perkin Trans. I , pp. 977-982
    • Crossley, R.1    Curran, A.C.W.2    Hill, D.G.3
  • 25
    • 37049104206 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. Part 6. Silylation vs. Thioamidation in the Reaction of Silyl Isothiocyanates with Organometallics: Influence of the Solvent and of the Substituents on Silicon
    • Crossley, R.; Shepherd, R. G. 5, 6, 7, 8-Tetrahydroquinolines. Part 6. Silylation vs. Thioamidation in the Reaction of Silyl Isothiocyanates with Organometallics: Influence of the Solvent and of the Substituents on Silicon. J. Chem. Soc., Perkin Trans. 1 1985, 1917-1920.
    • (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 1917-1920
    • Crossley, R.1    Shepherd, R.G.2
  • 26
    • 0017755294 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. 4. Antiulcer and Antisecretory Activity of 5, 6, 7, 8- Tetrahydroquinolinenitriles and -thioamides
    • Beattie, D. E.; Crossley, R.; Curran, A. C. W.; Dixon, G. T.; Hill, D. G.; Lawrence, A. E.; Shepherd, R. G. 5, 6, 7, 8-Tetrahydroquinolines. 4. Antiulcer and Antisecretory Activity of 5, 6, 7, 8- Tetrahydroquinolinenitriles and -thioamides. J. Med. Chem. 1977, 20, 714-718.
    • (1977) J. Med. Chem. , vol.20 , pp. 714-718
    • Beattie, D.E.1    Crossley, R.2    Curran, A.C.W.3    Dixon, G.T.4    Hill, D.G.5    Lawrence, A.E.6    Shepherd, R.G.7
  • 27
    • 37049099034 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. Part 7. Synthesis of 8-Cyano-5, 6, 7, 8-tetrahydroquinolines; Di-iso- propylcyanamide, a New Reagent for Cyanation of Organometallics
    • Crossley, R.; Shepherd, R. G. 5, 6, 7, 8-Tetrahydroquinolines. Part 7. Synthesis of 8-Cyano-5, 6, 7, 8-tetrahydroquinolines; Di-iso- propylcyanamide, a New Reagent for Cyanation of Organometallics. J. Chem. Soc., Perkin Trans I 1985, 2479-2481.
    • (1985) J. Chem. Soc., Perkin Trans I , pp. 2479-2481
    • Crossley, R.1    Shepherd, R.G.2
  • 28
    • 85022518194 scopus 로고
    • U. S. Pat. 5, 112, 832A
    • John Wyeth & Brother Ltd., U. S. Pat. 5, 112, 832A, 1992.
    • (1992)
  • 30
    • 0021274160 scopus 로고
    • Differential effects of putative lipoxygenase inhibitors on Arachidonic acid metabolism in cell-free and intact cell preparations
    • Chang, J.; Skowronek, M. D.; Cherney, M. L.; Lewis, A. J. Differential effects of putative lipoxygenase inhibitors on Arachidonic acid metabolism in cell-free and intact cell preparations. Inflammation 1984, 8, 143-155.
    • (1984) Inflammation , vol.8 , pp. 143-155
    • Chang, J.1    Skowronek, M.D.2    Cherney, M.L.3    Lewis, A.J.4
  • 31
    • 67249094291 scopus 로고
    • Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Anti-inflammatory drugs
    • Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Anti-inflammatory drugs. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
    • (1962) Proc. Soc. Exp. Biol. Med. , vol.111 , pp. 544-547
    • Winter, C.A.1    Risley, E.A.2    Nuss, G.W.3
  • 32
    • 0021252520 scopus 로고
    • The anti-inflammatory profile of (5H-dibenzo[A, D]-cyclohep- ten-5-ylidene) acetic acid (Wy-41, 770), an agent possessing weak prostaglandin synthetase inhibitory activity that is devoid of gastric side effects
    • Carlson, R. P.; Datko, L. J.; Chang, J.; Nielson, S. T.; Lewis, A. J. The anti-inflammatory profile of (5H-dibenzo[A, D]-cyclohep- ten-5-ylidene) acetic acid (Wy-41, 770), an agent possessing weak prostaglandin synthetase inhibitory activity that is devoid of gastric side effects. Agents Actions 1984, 14, 654-661.
    • (1984) Agents Actions , vol.14 , pp. 654-661
    • Carlson, R.P.1    Datko, L.J.2    Chang, J.3    Nielson, S.T.4    Lewis, A.J.5
  • 33
    • 0016654039 scopus 로고
    • Investigation of the vasodilator and anti-secretory role of prostaglandins in the rat gastric mucosa by use of non-steroidal anti-inflammatory drugs
    • Main, I. H. M.; Whittle, B. J. R. Investigation of the vasodilator and anti-secretory role of prostaglandins in the rat gastric mucosa by use of non-steroidal anti-inflammatory drugs. Br. J. Pharmacol. 1975, 53, 217-224.
    • (1975) Br. J. Pharmacol. , vol.53 , pp. 217-224
    • Main, I.H.M.1    Whittle, B.J.R.2
  • 34
    • 0025091871 scopus 로고
    • Design of an Antithrombotic- Antihypertensive Agent (Wy 27569). Synthesis and Evaluation of a Series of 2-Heteroaryl-Substituted Dihydropyridines
    • Archibald, J. L.; Bradley, G.; Opalko, A.; Ward, T. J.; White, J. C.; Ennis, C.; Shepperson, N. B. Design of an Antithrombotic- Antihypertensive Agent (Wy 27569). Synthesis and Evaluation of a Series of 2-Heteroaryl-Substituted Dihydropyridines. J. Med. Chem. 1990, 33, 646-652.
    • (1990) J. Med. Chem. , vol.33 , pp. 646-652
    • Archibald, J.L.1    Bradley, G.2    Opalko, A.3    Ward, T.J.4    White, J.C.5    Ennis, C.6    Shepperson, N.B.7
  • 35
    • 77956831742 scopus 로고
    • Thromboxane Synthase Inhibitors and Receptor Antagonists
    • Bristol, J. A., Ed.; Academic Press: New York
    • Collington, E. W.; Finch, H. Thromboxane Synthase Inhibitors and Receptor Antagonists. In Annual Reports in Medicinal Chemistry, Bristol, J. A., Ed.; Academic Press: New York, 1990; Vol. 25, pp 99-108.
    • (1990) Annual Reports in Medicinal Chemistry , vol.25 , pp. 99-108
    • Collington, E.W.1    Finch, H.2
  • 37
    • 1642480401 scopus 로고
    • Reaction d’addicion de Michael entre aldehyde α-ethyleniques et cetones saturees. (Michael addition reaction between α-ethylenic aldehydes and saturated ketones.)
    • Colonge, J.; Dreux, J.; Thiers, M. Reaction d’addicion de Michael entre aldehyde α-ethyleniques et cetones saturees. (Michael addition reaction between α-ethylenic aldehydes and saturated ketones.) Compt. Rend. 1957, 244, 89-90.
    • (1957) Compt. Rend. , vol.244 , pp. 89-90
    • Colonge, J.1    Dreux, J.2    Thiers, M.3
  • 38
    • 37049102221 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. Part III. Synthesis of 5, 6, 7, 8-Tetrahydroquinoline-8-thiocar- boxamides
    • Curran, A. C. W.; Shepherd, R. G. 5, 6, 7, 8-Tetrahydroquinolines. Part III. Synthesis of 5, 6, 7, 8-Tetrahydroquinoline-8-thiocar- boxamides. J. Chem. Soc., Perkin Trans. 1 1976, 983-986.
    • (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 983-986
    • Curran, A.C.W.1    Shepherd, R.G.2
  • 39
    • 37049098560 scopus 로고
    • 5, 6, 7, 8-Tetrahydroquinolines. Part I. A Novel Synthesis of 7, 8-Dihydro-quinolin-5 (6H)-ones
    • Curran, A. C. W. 5, 6, 7, 8-Tetrahydroquinolines. Part I. A Novel Synthesis of 7, 8-Dihydro-quinolin-5 (6H)-ones J. Chem. Soc., Perkin Trans. 1 1976, 975-977.
    • (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 975-977
    • Curran, A.C.W.1
  • 40
    • 84932101740 scopus 로고
    • Tetrahydroacridine, Octahydroacridine, and their derivatives
    • Perkin, W. H., Jr.; Sedwick, W. H. Tetrahydroacridine, Octahydroacridine, and their derivatives. J. Chem. Soc. 1924, 2437-2451.
    • (1924) J. Chem. Soc. , pp. 2437-2451
    • Perkin, W.H.1    Sedwick, W.H.2
  • 41
    • 84918018294 scopus 로고
    • Uber Tetrahydroacridin und eine neue Acridin-Synthese. (Tetrahydroacridine and a new Acridine Synthesis.)
    • Borsche, W. Uber Tetrahydroacridin und eine neue Acridin-Synthese. (Tetrahydroacridine and a new Acridine Synthesis.) Chem. Ber. 1908, 41, 2203-2208.
    • (1908) Chem. Ber. , vol.41 , pp. 2203-2208
    • Borsche, W.1
  • 42
    • 20444415951 scopus 로고
    • Cycloparaffines condensed with the heterocyclic rings. Part XIV. Synthesis of 6-methyl- 2, 3-cycloalkenopyridines
    • Epsztajn, J.; Hahn, W. E.; Tosik, B. K. Cycloparaffines condensed with the heterocyclic rings. Part XIV. Synthesis of 6-methyl- 2, 3-cycloalkenopyridines. Roczniki Chem. 1970, 44, 431-439.
    • (1970) Roczniki Chem. , vol.44 , pp. 431-439
    • Epsztajn, J.1    Hahn, W.E.2    Tosik, B.K.3


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