메뉴 건너뛰기




Volumn 43, Issue 10, 2000, Pages 2040-2048

Novel antiarthritic agents with 1,2-isothiazolidine-1-,1-dioxide (γ- sultam) skeleton: Cytokine suppressive dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase

Author keywords

[No Author keywords available]

Indexed keywords

3 (3,5 DI TERT BUTYL 4 HYDROXYBENZYLIDENE) 1 METHOXY 2 PYRROLIDINONE; 4 (3,5 DI TERT BUTYL 4 HYDROXYPHENYL) 2 METHYL 1,2 OXAZIN 3 ONE; ANTIRHEUMATIC AGENT; CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; INTERLEUKIN 1; LIPOXYGENASE INHIBITOR; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; S 2474; SATIGREL; THIAZOLIDINE DERIVATIVE;

EID: 0034075728     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9906015     Document Type: Article
Times cited : (172)

References (51)
  • 1
    • 0031787631 scopus 로고    scopus 로고
    • Antiinflammatory drugs and their mechanism of action
    • Vane, J. R.; Botting, R. M. Antiinflammatory Drugs and Their Mechanism of Action. Inflammation Res. 1998, 47 (Suppl. 2), S78-S87.
    • (1998) Inflammation Res. , vol.47 , Issue.2 SUPPL.
    • Vane, J.R.1    Botting, R.M.2
  • 2
    • 0026443983 scopus 로고
    • NSAIDS, ulcers, and prostaglandins
    • (a) Kimmey, M. B. NSAIDS, Ulcers, and Prostaglandins. J. Rheumatol. 1992, 19, 68-73.
    • (1992) J. Rheumatol. , vol.19 , pp. 68-73
    • Kimmey, M.B.1
  • 3
    • 0017578432 scopus 로고
    • On the synthesis of prostaglandins by human gastric mucosa and its modification by drugs
    • (b) Peskar, B. M. On the Synthesis of Prostaglandins by Human Gastric Mucosa and its Modification by Drugs. Biochim. Biophys. Acta. 1977, 487, 307-314.
    • (1977) Biochim. Biophys. Acta , vol.487 , pp. 307-314
    • Peskar, B.M.1
  • 4
    • 0020858787 scopus 로고
    • Protective effects of prostaglandins against gastric mucosal damage: Current knowledge and proposed mechanisms
    • Miller, T. A. Protective Effects of Prostaglandins against Gastric Mucosal Damage: Current Knowledge and Proposed Mechanisms. Am. J. Physiol. 1983, 245, G601-G623.
    • (1983) Am. J. Physiol. , vol.245
    • Miller, T.A.1
  • 5
    • 0025754779 scopus 로고
    • Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing
    • (a) Xie, W.; Chipman, J. G.; Robertson, D. L.; Erikson, R. L.; Simmons, D. L. Expression of a Mitogen-Responsive Gene Encoding Prostaglandin Synthase is Regulated by mRNA Splicing. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2692-2696.
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 2692-2696
    • Xie, W.1    Chipman, J.G.2    Robertson, D.L.3    Erikson, R.L.4    Simmons, D.L.5
  • 6
    • 0025871150 scopus 로고
    • TIS 10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue
    • (b) Kujubu, D. A.; Fletcher, B. S.; Varnum, B. C.; Lim, R. W.; Herschman, H. R. TIS 10, a Phorbol Ester Tumor Promoter-inducible mRNA from Swiss 3T3 cells, Encodes a Novel Prostaglandin Synthase/Cyclooxygenase Homologue. J. Biol. Chem. 1991, 266, 12866-12872.
    • (1991) J. Biol. Chem. , vol.266 , pp. 12866-12872
    • Kujubu, D.A.1    Fletcher, B.S.2    Varnum, B.C.3    Lim, R.W.4    Herschman, H.R.5
  • 10
    • 0021223574 scopus 로고
    • Pharmacological properties of a new antiinflammatory compound, α-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-γ-butyrolactone (KME-4), and its inhibitory effects on prostaglandin synthetase and 5-lipoxygenase
    • Hidaka, T.; Hosoe, K.; Ariki, Y.; Takeo, K.; Yamashita, T.; Katsumi, I.; Kondo, H.; Yamashita, K.; Watanabe, K. Pharmacological Properties of a New Antiinflammatory Compound, α-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-γ-butyrolactone (KME-4), and its Inhibitory Effects on Prostaglandin Synthetase and 5-Lipoxygenase. Jpn. J. Pharmacol. 1984, 36, 77-85.
    • (1984) Jpn. J. Pharmacol. , vol.36 , pp. 77-85
    • Hidaka, T.1    Hosoe, K.2    Ariki, Y.3    Takeo, K.4    Yamashita, T.5    Katsumi, I.6    Kondo, H.7    Yamashita, K.8    Watanabe, K.9
  • 11
    • 0023572184 scopus 로고
    • Synthesis and antiinflammatory activities of 3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones
    • Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y.; Yamada, K.; Yamatsu, I.; Katayama, K. Synthesis and Antiinflammatory Activities of 3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones. J. Med. Chem. 1987, 30, 1995-1998.
    • (1987) J. Med. Chem. , vol.30 , pp. 1995-1998
    • Ikuta, H.1    Shirota, H.2    Kobayashi, S.3    Yamagishi, Y.4    Yamada, K.5    Yamatsu, I.6    Katayama, K.7
  • 13
    • 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, C. D.; 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, C.D.7    Schrier, D.J.8    Dyer, R.D.9
  • 14
    • 0025125827 scopus 로고
    • Leukotrienes and inflammation
    • (a) Brain, S. D.; Williams, T. J. Leukotrienes and Inflammation. Pharmacol. Ther. 1990, 46, 57-66.
    • (1990) Pharmacol. Ther. , vol.46 , pp. 57-66
    • Brain, S.D.1    Williams, T.J.2
  • 15
    • 0026579528 scopus 로고
    • Pharmacological investigation of the role of leukotrienes in the pathogenesis of experimental NSAID gastropathy
    • (b) Vaananen, P. M.; Keenan, C. M.; Grisham, M. B.; Wallace, J. L. Pharmacological Investigation of the Role of Leukotrienes in the Pathogenesis of Experimental NSAID Gastropathy. Inflammation 1992, 16, 227-240.
    • (1992) Inflammation , vol.16 , pp. 227-240
    • Vaananen, P.M.1    Keenan, C.M.2    Grisham, M.B.3    Wallace, J.L.4
  • 17
    • 0026742483 scopus 로고
    • Indomethacin-induced leukocyte adhesion in mesenteric venules: Role of lipoxygenase products
    • (d) Asako, H.; Kubes, P.; Wallace, J.; Gaginella, T.; Wolf, R. E.; Granger, D. N. Indomethacin-Induced Leukocyte Adhesion in Mesenteric Venules: Role of Lipoxygenase Products. Am. J. Physiol. 1992, 262, G903-G908.
    • (1992) Am. J. Physiol. , vol.262
    • Asako, H.1    Kubes, P.2    Wallace, J.3    Gaginella, T.4    Wolf, R.E.5    Granger, D.N.6
  • 18
    • 0030743785 scopus 로고    scopus 로고
    • The mechanisms of action of diseese-modifying antirheumatic drugs: A review with emphasis on macrophage signal transduction and the induction of proinflammatory cytokines
    • Bondeson, J. The Mechanisms of Action of Diseese-Modifying Antirheumatic Drugs: A Review with Emphasis on Macrophage Signal Transduction and the Induction of Proinflammatory Cytokines. Gen. Pharmacol. 1997, 29, 127-150.
    • (1997) Gen. Pharmacol. , vol.29 , pp. 127-150
    • Bondeson, J.1
  • 19
    • 0028568363 scopus 로고
    • Tenidap: A novel cytokine-modulating antirheumatic drug for the treatment of rheumatoid arthritis
    • (a) Bleedverd, F. Tenidap: A Novel Cytokine-Modulating Antirheumatic Drug for the Treatment of Rheumatoid Arthritis. Scand. J. Rheumatol. 1994, 23, 31-44.
    • (1994) Scand. J. Rheumatol. , vol.23 , pp. 31-44
    • Bleedverd, F.1
  • 20
    • 0029155425 scopus 로고
    • Tenidap
    • (b) Madhok, K. Tenidap. Lancet 1995, 346, 481-485.
    • (1995) Lancet , vol.346 , pp. 481-485
    • Madhok, K.1
  • 21
    • 0030250824 scopus 로고    scopus 로고
    • Effects of tenidap on intracellular signal transduction and the induction of proinflammatory cytokines: A review
    • (c) Bondeson, J. Effects of Tenidap on Intracellular Signal Transduction and the Induction of Proinflammatory Cytokines: A Review Gen. Pharmacol. 1996, 27, 943-956.
    • (1996) Gen. Pharmacol. , vol.27 , pp. 943-956
    • Bondeson, J.1
  • 22
    • 0342818553 scopus 로고    scopus 로고
    • Oct. 17
    • (a) Marketletter Oct. 17, 1996.
    • (1996) Marketletter
  • 23
    • 0342818556 scopus 로고    scopus 로고
    • Feb. 02
    • (b) Marketletter Feb. 02, 1998.
    • (1998) Marketletter
  • 24
    • 0023749034 scopus 로고
    • Inhibition by probucol of interleukin 1 secretion and its implication in atherosclerosis
    • (a) Ku, G.; Doherty, N. S.; Wolos, J. A.; Jackson, R. L. Inhibition by Probucol of Interleukin 1 secretion and its Implication in Atherosclerosis. Am. J. Cardiol. 1988, 62, 77B-81B.
    • (1988) Am. J. Cardiol. , vol.62
    • Ku, G.1    Doherty, N.S.2    Wolos, J.A.3    Jackson, R.L.4
  • 25
    • 0026058246 scopus 로고
    • Inhibition of IL-1β expression in THP-1 cells by probucol and tocopherol
    • (b) Akeson, A. L.; Woods, C. W.; Mosher, L. B.; Thomas, C. E.; Jackson, R. L. Inhibition of IL-1β Expression in THP-1 Cells by Probucol and tocopherol. Atherosclerosis 1991, 86, 261-270.
    • (1991) Atherosclerosis , vol.86 , pp. 261-270
    • Akeson, A.L.1    Woods, C.W.2    Mosher, L.B.3    Thomas, C.E.4    Jackson, R.L.5
  • 26
    • 0342383663 scopus 로고
    • Probucol inhibits IL-1β synthesis by minimally modified LDL-stimulated human mononuclear cells
    • (c) Woolaghan, E.; Li, S.-R.; Forster, L.; Änggard, E. E.; Ferns, G. A. A. Probucol Inhibits IL-1β Synthesis by Minimally Modified LDL-Stimulated Human Mononuclear Cells. Clin. Sci. 1995, 88, 4-5.
    • (1995) Clin. Sci. , vol.88 , pp. 4-5
    • Woolaghan, E.1    Li, S.-R.2    Forster, L.3    Änggard, E.E.4    Ferns, G.A.A.5
  • 27
    • 0009463946 scopus 로고
    • Syntheses and facile cleavage of five-membered ring sultams
    • Erman, W. F.; Kretschmar, H. C. Syntheses and Facile Cleavage of Five-Membered Ring Sultams. J. Org. Chem. 1961, 26, 4841-4850.
    • (1961) J. Org. Chem. , vol.26 , pp. 4841-4850
    • Erman, W.F.1    Kretschmar, H.C.2
  • 28
    • 0342383666 scopus 로고    scopus 로고
    • note
    • 2 of Z-isomers. Vinyl protons of Z-isomers shifted higher than those of the corresponding E-isomers in NMR study.
  • 29
    • 0343253169 scopus 로고    scopus 로고
    • note
    • X-ray crystallographic data of 10b and 12b are given in the Supporting Information.
  • 30
    • 0042952293 scopus 로고
    • Kinetics and mechanism of hydrolysis of aryl N-methoxycarbamates and their derivatives
    • (a) Mindl, J.; Šterna, V. Kinetics and Mechanism of Hydrolysis of Aryl N-Methoxycarbamates and Their Derivatives. Coll. Czech. Chem. Commun. 1983, 48, 900-905.
    • (1983) Coll. Czech. Chem. Commun. , vol.48 , pp. 900-905
    • Mindl, J.1    Šterna, V.2
  • 31
    • 0004475165 scopus 로고
    • Some new hydroxy-urethanes and chromo-isomeric silver salts of their acyl derivatives. III
    • (b) Oesper, R. E.; Broker, W. Some New Hydroxy-Urethanes and Chromo-Isomeric Silver Salts of Their Acyl Derivatives. III. J. Am. Chem. Soc. 1925, 47, 2606-2608.
    • (1925) J. Am. Chem. Soc. , vol.47 , pp. 2606-2608
    • Oesper, R.E.1    Broker, W.2
  • 32
    • 0007884460 scopus 로고
    • N-hydrox'y aryl carbamates. A class of hydroxamic acids which form stable phosphorylated and sulfated derivatives
    • (c) Steinberg, G. M.; Bolger, J. N-Hydrox'y Aryl Carbamates. A Class of Hydroxamic Acids Which Form Stable Phosphorylated and Sulfated Derivatives. J. Org. Chem. 1956, 21, 660-662.
    • (1956) J. Org. Chem. , vol.21 , pp. 660-662
    • Steinberg, G.M.1    Bolger, J.2
  • 33
    • 0343688857 scopus 로고
    • Chloroalkanesulfonyl chloride
    • (a) Wolfgang, K. Chloroalkanesulfonyl Chloride. Chem. Abstr. 1969, 71, 101310x.
    • (1969) Chem. Abstr. , vol.71
    • Wolfgang, K.1
  • 34
    • 0343253165 scopus 로고    scopus 로고
    • Ger. Patent Application 1300933, 1969
    • (b) Ger. Patent Application 1300933, 1969.
  • 35
    • 0023277836 scopus 로고
    • Effect of the novel non-steroidal antiinflammatory agent N-methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one on in vitro generation of some inflammatory mediators
    • Shirota, H.; Kobayashi, S.; Terao, K.; Sakuma, Y.; Yamada, K.; Ikuta, H.; Yamagishi, Y.; Yamatsu, I.; Katayama, K. Effect of the Novel Non-Steroidal Antiinflammatory Agent N-Methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one on In Vitro Generation of Some Inflammatory Mediators. Arzneim.-Forsch. / Drug. Res. 1987, 37, 936-940.
    • (1987) Arzneim.-Forsch. / Drug. Res. , vol.37 , pp. 936-940
    • Shirota, H.1    Kobayashi, S.2    Terao, K.3    Sakuma, Y.4    Yamada, K.5    Ikuta, H.6    Yamagishi, Y.7    Yamatsu, I.8    Katayama, K.9
  • 37
    • 0025963002 scopus 로고
    • The human leukemia cell line, THP-1: A multifacetted model for the study of monocyte-macrophage differentiation
    • Auwerx, J. The Human Leukemia Cell Line, THP-1: A Multifacetted Model for the Study of Monocyte-Macrophage Differentiation. Experientia 1991, 47, 22-30.
    • (1991) Experientia , vol.47 , pp. 22-30
    • Auwerx, J.1
  • 38
    • 67249094291 scopus 로고
    • Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. (27849)
    • (a) Winter, C. A.; Rilsey, E. A.; Nuss, G. W. Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Antiinflammatory Drugs. (27849) Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
    • (1962) Proc. Soc. Exp. Biol. Med. , vol.111 , pp. 544-547
    • Winter, C.A.1    Rilsey, E.A.2    Nuss, G.W.3
  • 39
    • 0023198548 scopus 로고
    • Pharmacological properties of the novel non-steroidal antiinflammatory agent N-methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-pyrrolidin-2-one
    • (b) Shirota, H.; Chiba, K.; Ono, H.; Yamamoto, H.; Kobayashi, S.; Terao, K.; Ikuta, H.; Yamatsu, I.; Katayama, K. Pharmacological Properties of the Novel Non-Steroidal Antiinflammatory Agent N-Methoxy-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)-pyrrolidin-2-one. Arzneim.-Forsch. / Drug. Res. 1987, 37, 930-936.
    • (1987) Arzneim.-Forsch. / Drug. Res. , vol.37 , pp. 930-936
    • Shirota, H.1    Chiba, K.2    Ono, H.3    Yamamoto, H.4    Kobayashi, S.5    Terao, K.6    Ikuta, H.7    Yamatsu, I.8    Katayama, K.9
  • 40
    • 0014589773 scopus 로고
    • Comparative bioassay of drugs in adjuvant-induced arthritis in rats: Flufenamic acid, mefenamic acid, and phenylbutazone
    • (a) Winder, C. V.; Lembke, L. A.; Stephens, M. D. Comparative Bioassay of Drugs in Adjuvant-Induced Arthritis in Rats: Flufenamic Acid, Mefenamic Acid, and Phenylbutazone. Arthritis Rheum. 1969, 12, 472-482.
    • (1969) Arthritis Rheum. , vol.12 , pp. 472-482
    • Winder, C.V.1    Lembke, L.A.2    Stephens, M.D.3
  • 41
    • 0015031311 scopus 로고
    • Adjuvant-induced arthritis in rats I. Temporal relationship of physiological, biochemical, and hemotological parameters (35392)
    • (b) Walz, D. T.; Dimartino, M. J.; Kuch, J. H.; Zuccarello, W. Adjuvant-Induced Arthritis in Rats I. Temporal Relationship of Physiological, Biochemical, and hemotological Parameters (35392). Proc. Soc. Exp. Biol. Med. 1971, 136, 907-910.
    • (1971) Proc. Soc. Exp. Biol. Med. , vol.136 , pp. 907-910
    • Walz, D.T.1    Dimartino, M.J.2    Kuch, J.H.3    Zuccarello, W.4
  • 42
    • 0032540212 scopus 로고    scopus 로고
    • Comparison of cyclooxygenase-1 and -2 inhibitory activities of various nonsteroidal antiinflammatory drugs using human platelets and synovial cells
    • Kawai, S.; Nishida, S.; Kato, M.; Furumaya, Y.; Okamoto, R.; Koshino, T.; Mizushima, Y. Comparison of Cyclooxygenase-1 and -2 Inhibitory Activities of Various Nonsteroidal Antiinflammatory Drugs Using Human Platelets and Synovial Cells. Eur. J. Pharmacol. 1998, 347, 87-94.
    • (1998) Eur. J. Pharmacol. , vol.347 , pp. 87-94
    • Kawai, S.1    Nishida, S.2    Kato, M.3    Furumaya, Y.4    Okamoto, R.5    Koshino, T.6    Mizushima, Y.7
  • 44
    • 0342818547 scopus 로고    scopus 로고
    • note
    • Neither 12b nor 10b could be detected in the plasma after oral administration of 12b. Furthermore, orally active 10b could not be detected in the plasma after intravanous injection of 12b to nonfasted rats at a dose of 1 mg/kg. Compound 12b could not be thought to isomerize under the conditions of this assay. However, 12b was irreversibly isomerized slowly to 10b in the MeOH solution at room temperature.
  • 45
    • 0028089109 scopus 로고
    • NS 398, a new antiinflammatory agent, selectively inhibits prostaglandin G/H synthase/cyclooxygenase (COX-2) activity in vitro
    • Futaki, N.; Takahashi, S.; Yokoyama, M.; Arai, I.; Higuchi, S.; Otomo, S. NS 398, a New Antiinflammatory Agent, Selectively Inhibits Prostaglandin G/H Synthase/Cyclooxygenase (COX-2) Activity In Vitro. Prostaglandins 1994, 47, 55-59.
    • (1994) Prostaglandins , vol.47 , pp. 55-59
    • Futaki, N.1    Takahashi, S.2    Yokoyama, M.3    Arai, I.4    Higuchi, S.5    Otomo, S.6
  • 47
    • 0017618224 scopus 로고
    • Cyclic adenosine 3′, 5′-monophosphate inhibits the availability of arachidonate to prostaglandin synthetase in human platelet suspensions
    • Minkes, M.; Stanford, N.; Chi, M. M-Y.; Roth, G. J.; Raz, A.; Needleman, P.; Majerus, P. W. Cyclic Adenosine 3′, 5′-Monophosphate Inhibits the Availability of Arachidonate to Prostaglandin Synthetase in Human Platelet Suspensions. J. Clin. Invest. 1977, 59, 449-454.
    • (1977) J. Clin. Invest. , vol.59 , pp. 449-454
    • Minkes, M.1    Stanford, N.2    Chi, M.M.-Y.3    Roth, G.J.4    Raz, A.5    Needleman, P.6    Majerus, P.W.7
  • 48
    • 0013546153 scopus 로고
    • Production of collagenase and prostaglandins by isolated adherent rheumatoid synovial cells
    • (a) Dayer, J.-M.; Krane, S. M.; Russell, R. G. G.; Robinson, D. R. Production of Collagenase and Prostaglandins by Isolated Adherent Rheumatoid Synovial Cells. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 945-949.
    • (1976) Proc. Natl. Acad. Sci. U.S.A. , vol.73 , pp. 945-949
    • Dayer, J.-M.1    Krane, S.M.2    Russell, R.G.G.3    Robinson, D.R.4
  • 50
    • 0342383660 scopus 로고    scopus 로고
    • Japanese Patent Application 209564, 1985
    • Japanese Patent Application 209564, 1985.
  • 51
    • 0343688853 scopus 로고    scopus 로고
    • Japanese Patent Application 268, 1990
    • Japanese Patent Application 268, 1990.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.