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Volumn 41, Issue 10, 1998, Pages 1729-1740

Novel thieno[2,3-d][1,3]oxazin-4-ones as inhibitors of human leukocyte elastase

Author keywords

[No Author keywords available]

Indexed keywords

ELASTASE INHIBITOR; THIENO[2,3 D][1.3]OXAZIN 4 ONE; UNCLASSIFIED DRUG;

EID: 0032493051     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9708341     Document Type: Article
Times cited : (64)

References (50)
  • 1
    • 0029897335 scopus 로고    scopus 로고
    • Prospects for the Development of New Drugs for the Therapy of Respiratory Diseases
    • (a) Whelan, C. J. Prospects for the Development of New Drugs for the Therapy of Respiratory Diseases. Drugs Today 1996, 32, 295-311.
    • (1996) Drugs Today , vol.32 , pp. 295-311
    • Whelan, C.J.1
  • 3
    • 0028926740 scopus 로고
    • Serine Proteinase in Articular Cartilage, Subchondral Bone Marrow and Synovial Fluid in Human Osteoarthritis and Rheumatoid Arthritis
    • (c) Nakagawa, T.; Momohara, S.; Fujita, K.; Kodama, T.; Yamada, H.; Nagai, Y. Serine Proteinase in Articular Cartilage, Subchondral Bone Marrow and Synovial Fluid in Human Osteoarthritis and Rheumatoid Arthritis. Biomed. Res. 1995, 16, 11-20.
    • (1995) Biomed. Res. , vol.16 , pp. 11-20
    • Nakagawa, T.1    Momohara, S.2    Fujita, K.3    Kodama, T.4    Yamada, H.5    Nagai, Y.6
  • 4
    • 0029268446 scopus 로고
    • Granulocyte Elastase in Gingival Crevicular Fluid: Improved Monitoring of the Site-Specific Response to Treatment in Patients with Destructive Periodontitis
    • (d) Jin, L. J.; Boeder, P.-O.; Aaasman, B.; Bergstroem, K. Granulocyte Elastase in Gingival Crevicular Fluid: Improved Monitoring of the Site-Specific Response to Treatment in Patients with Destructive Periodontitis. J. Clin. Periodontol 1995, 22, 240-246.
    • (1995) J. Clin. Periodontol , vol.22 , pp. 240-246
    • Jin, L.J.1    Boeder, P.-O.2    Aaasman, B.3    Bergstroem, K.4
  • 5
    • 77956791952 scopus 로고
    • Human Leukocyte Elastase Inhibitors
    • (a) Hlasta, D. J.; Pagini, E. D. Human Leukocyte Elastase Inhibitors. Annu. Rep, Med. Chem. 1994, 29, 195-204.
    • (1994) Annu. Rep, Med. Chem. , vol.29 , pp. 195-204
    • Hlasta, D.J.1    Pagini, E.D.2
  • 6
    • 0028282060 scopus 로고
    • Synthetic Inhibitors of Elastase
    • (b) Edwards, P. D.; Bernstein, P. R. Synthetic Inhibitors of Elastase. Med. Res. Rev. 1994, 14, 127-194.
    • (1994) Med. Res. Rev. , vol.14 , pp. 127-194
    • Edwards, P.D.1    Bernstein, P.R.2
  • 8
    • 0024535210 scopus 로고
    • Mechanism-Based Isocoumarin Inhibitors for Serine Proteases: Use of Active Site Structure and Substrate Specificity in Inhibitor Design
    • Powers, J. C.; Kam, C.-M.; Narasimhan, L.; Oleksyszyn, J.; Hernandez, M. A.; Ueda, T. Mechanism-Based Isocoumarin Inhibitors for Serine Proteases: Use of Active Site Structure and Substrate Specificity in Inhibitor Design. J. Celt. Biochem. 1989, 39, 33-46.
    • (1989) J. Celt. Biochem. , vol.39 , pp. 33-46
    • Powers, J.C.1    Kam, C.-M.2    Narasimhan, L.3    Oleksyszyn, J.4    Hernandez, M.A.5    Ueda, T.6
  • 9
    • 0024571818 scopus 로고
    • Human Leukocyte and Porcine Pancreatic Elastase: X-ray Crystal Structures, Mechanism, Substrate Specificity, and Mechanism-Based Inhibitors
    • Bode, W.; Meyer, E.; Powers, J. C. Human Leukocyte and Porcine Pancreatic Elastase: X-ray Crystal Structures, Mechanism, Substrate Specificity, and Mechanism-Based Inhibitors. Biochemistry 1989, 28, 1951-1963.
    • (1989) Biochemistry , vol.28 , pp. 1951-1963
    • Bode, W.1    Meyer, E.2    Powers, J.C.3
  • 11
    • 0026589236 scopus 로고
    • Effect of the 7-Amino Substituent on the Inhibitory Potency of Mechanism-Based Isocoumarin Inhibitors for Porcine Pancreatic and Human Neutrophil Elastases; A 1.85-A X-ray Structure of the Complex between Porcine Pancreatic Elastase and 7-[(N-Tosyphenylalanyl)amino]4-chloro-3-methoxyisocoumarin
    • Hernandez, M. A.; Powers, J. C.; Glinski, J.; Oleksyszyn, J.; Vijayalakshmi, J.; Meyer, E. F. Effect of the 7-Amino Substituent on the Inhibitory Potency of Mechanism-Based Isocoumarin Inhibitors for Porcine Pancreatic and Human Neutrophil Elastases; A 1.85-A X-ray Structure of the Complex between Porcine Pancreatic Elastase and 7-[(N-Tosyphenylalanyl)amino]4-chloro-3-methoxyisocoumarin. J. Med. Chem. 1992, 35, 1121-1129.
    • (1992) J. Med. Chem. , vol.35 , pp. 1121-1129
    • Hernandez, M.A.1    Powers, J.C.2    Glinski, J.3    Oleksyszyn, J.4    Vijayalakshmi, J.5    Meyer, E.F.6
  • 12
    • 0024333382 scopus 로고
    • Inhibition of Human Leukocyte Elastase by Derivatives of N-Hydroxysuccinimide. A Structure-Activity-Relationship Study
    • Groutas, W. C.; Brubaker, M. J.; Stanga, M. A.; Castrisos, J. C.; Crowley, J. P.; Schatz, E. J. Inhibition of Human Leukocyte Elastase by Derivatives of N-Hydroxysuccinimide. A Structure-Activity-Relationship Study. J. Med. Chem. 1989, 32, 1607-1611.
    • (1989) J. Med. Chem. , vol.32 , pp. 1607-1611
    • Groutas, W.C.1    Brubaker, M.J.2    Stanga, M.A.3    Castrisos, J.C.4    Crowley, J.P.5    Schatz, E.J.6
  • 13
    • 0029010868 scopus 로고
    • Design, Synthesis and Biological Evaluation of Succinimide Derivatives as Potential Mechanism-Based Inhibitors of Human Leukocyte Elastase, Cathepsin G and Proteinase 3
    • Groutas, W. C.; Brubaker, M. J.; Chong, L. S.; Venkataraman, R.; Huang, H.; Epp, J. B.; Kuang, R.; Hoidal, J. R. Design, Synthesis and Biological Evaluation of Succinimide Derivatives as Potential Mechanism-Based Inhibitors of Human Leukocyte Elastase, Cathepsin G and Proteinase 3. Bioorg. Med. Chem. 1995,4, 375-381.
    • (1995) Bioorg. Med. Chem. , vol.4 , pp. 375-381
    • Groutas, W.C.1    Brubaker, M.J.2    Chong, L.S.3    Venkataraman, R.4    Huang, H.5    Epp, J.B.6    Kuang, R.7    Hoidal, J.R.8
  • 14
    • 0028144987 scopus 로고
    • N-(Sulfonyloxy)phthalimides and Analogues Are Potent Inactivators of Serine Proteases
    • Neumann, U.; Gütschow, M. N-(Sulfonyloxy)phthalimides and Analogues Are Potent Inactivators of Serine Proteases. J. Biol. Chem. 1994, 269, 21561-21567.
    • (1994) J. Biol. Chem. , vol.269 , pp. 21561-21567
    • Neumann, U.1    Gütschow, M.2
  • 21
    • 0015915996 scopus 로고
    • Inactivation of α-Chymotrypsin by a Bifunctional Reagent, 2-Bromomethyl-3, lbenzoxazin-4-on
    • Alazard, R.; Bechet, J.-J.; Dupaix, A.; Yon, J. Inactivation of α-Chymotrypsin by a Bifunctional Reagent, 2-Bromomethyl-3, lbenzoxazin-4-on. Biochim. Biophys. Acta 1973, 309, 379-396.
    • (1973) Biochim. Biophys. Acta , vol.309 , pp. 379-396
    • Alazard, R.1    Bechet, J.-J.2    Dupaix, A.3    Yon, J.4
  • 22
    • 0019962491 scopus 로고
    • A New Class of Heterocyclic Serine Protease Inhibitors. Inhibition of Human Leukocyte Elastase, Porcine Pancreatic Elastase, Cathepsin G, and Bovine Chymotrypsin Aa with Substituted Benzoxazinones, Quinazolines, and Anthranilates
    • Teshima, T.; Griffin, J. C.; Powers, J. C. A New Class of Heterocyclic Serine Protease Inhibitors. Inhibition of Human Leukocyte Elastase, Porcine Pancreatic Elastase, Cathepsin G, and Bovine Chymotrypsin Aa with Substituted Benzoxazinones, Quinazolines, and Anthranilates. J. Biol. Chem. 1982, 257, 5085-5091.
    • (1982) J. Biol. Chem. , vol.257 , pp. 5085-5091
    • Teshima, T.1    Griffin, J.C.2    Powers, J.C.3
  • 23
    • 0021759418 scopus 로고
    • Suicide Inactivation of Chymotrypsin by Benzoxazinones
    • Hedstrom, L.; Moorman, A. R.; Dobbs, J.; Abeles, R. H. Suicide Inactivation of Chymotrypsin by Benzoxazinones. Biochemistry 1984, 23, 1753-1759.
    • (1984) Biochemistry , vol.23 , pp. 1753-1759
    • Hedstrom, L.1    Moorman, A.R.2    Dobbs, J.3    Abeles, R.H.4
  • 24
    • 0028940374 scopus 로고
    • 3,l-Benzothiazin-4-ones and 3,l-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation
    • Neumann, U.; Gütschow, M. 3,l-Benzothiazin-4-ones and 3,l-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation. Bioorg. Chem. 1995, 23, 72-88.
    • (1995) Bioorg. Chem. , vol.23 , pp. 72-88
    • Neumann, U.1    Gütschow, M.2
  • 25
    • 0342276109 scopus 로고    scopus 로고
    • Inhibition of Cathepsin G by 4H3,l-Benzoxazin-4-ones
    • Gütschow, M.; Neumann, U. Inhibition of Cathepsin G by 4H3,l-Benzoxazin-4-ones. Bioorg. Med. Chem. 1997, 5, 1935-1942.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 1935-1942
    • Gütschow, M.1    Neumann, U.2
  • 29
    • 0026032732 scopus 로고
    • Inhibition of Chymotrypsin and Pancreatic Elastase by 4H-3, l-Benzoxazin-4-ones
    • Neumann, U.; Stürzebecher, J.; Leistner, S.; Vieweg, H. Inhibition of Chymotrypsin and Pancreatic Elastase by 4H-3, l-Benzoxazin-4-ones. J. Enzyme Inhib. 1991, 4, 227-232.
    • (1991) J. Enzyme Inhib. , vol.4 , pp. 227-232
    • Neumann, U.1    Stürzebecher, J.2    Leistner, S.3    Vieweg, H.4
  • 30
    • 0023239061 scopus 로고
    • Mechanism for Slow-Binding Inhibition of Human Leukocyte Elastase by Valine-Derived Benzoxazinones
    • Stein, R. L.; Strimpler, A. M.; Viscarello, B. R.; Wildonger, R. A.; Mauger, R. C.; Trainor, D. A. Mechanism for Slow-Binding Inhibition of Human Leukocyte Elastase by Valine-Derived Benzoxazinones. Biochemistry 1987, 26, 4126-4130.
    • (1987) Biochemistry , vol.26 , pp. 4126-4130
    • Stein, R.L.1    Strimpler, A.M.2    Viscarello, B.R.3    Wildonger, R.A.4    Mauger, R.C.5    Trainor, D.A.6
  • 31
    • 0023317381 scopus 로고
    • Design of Alternate Substrate Inhibitors of Serine Proteases. Synergistic Use of Alkyl Substitution to Impede Enzyme-Catalyzed Deacylation
    • Krantz, A.; Spencer, R. W.; Tarn, T. F.; Thomas, E.; Copp, L. J. Design of Alternate Substrate Inhibitors of Serine Proteases. Synergistic Use of Alkyl Substitution To Impede Enzyme-Catalyzed Deacylation. J. Med. Chem. 1987, 30, 589-591.
    • (1987) J. Med. Chem. , vol.30 , pp. 589-591
    • Krantz, A.1    Spencer, R.W.2    Tarn, T.F.3    Thomas, E.4    Copp, L.J.5
  • 32
    • 0025098316 scopus 로고
    • Design and Synthesis of 4H-3,1Benzoxazin-4-ones as Potent Alternate Substrate Inhibitors of Human Leukocyte Elastase
    • Krantz, A.; Spencer, R. W.; Tarn, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. Design and Synthesis of 4H-3,1Benzoxazin-4-ones as Potent Alternate Substrate Inhibitors of Human Leukocyte Elastase. J. Med. Chem. 1990, 33, 464-479.
    • (1990) J. Med. Chem. , vol.33 , pp. 464-479
    • Krantz, A.1    Spencer, R.W.2    Tarn, T.F.3    Liak, T.J.4    Copp, L.J.5    Thomas, E.M.6    Rafferty, S.P.7
  • 33
    • 0027428786 scopus 로고
    • 5-Methyl-4H-3,1-benzoxazin-4-one Derivatives: Specific Inhibitors of Human Leukocyte Elastase
    • Uejima, Y.; Kokubo, M.; Oshida, J.-L; Kawabata, H.; Kato, Y.; Fujii, K. 5-Methyl-4H-3,1-benzoxazin-4-one Derivatives: Specific Inhibitors of Human Leukocyte Elastase. J. Pharmacol. Exp. Ther. 1993, 265, 516-523.
    • (1993) J. Pharmacol. Exp. Ther. , vol.265 , pp. 516-523
    • Uejima, Y.1    Kokubo, M.2    Oshida, J.-L.3    Kawabata, H.4    Kato, Y.5    Fujii, K.6
  • 34
    • 0027956209 scopus 로고
    • Inhibition of Human Sputum Elastase by 7-Substituted 5-Methyl-2-isopropylamino-4H-3, l-benzoxazin-4-ones
    • Uejima, Y.; Oshida, J.-L; Kawabata, H.; Kokubo, M.; Kato, Y.; Fuju, K. Inhibition of Human Sputum Elastase by 7-Substituted 5-Methyl-2-isopropylamino-4H-3, l-benzoxazin-4-ones. Biochem. Pharmacol. 1994, 48, 426-428.
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 426-428
    • Uejima, Y.1    Oshida, J.-L.2    Kawabata, H.3    Kokubo, M.4    Kato, Y.5    Fuju, K.6
  • 35
    • 84860875380 scopus 로고
    • 2-Aminothiophenes from Methylene-Active Nitriles, Carbonyl Compounds, and Sulfur
    • Gewald, K.; Schinke, E.; Böttcher, H. 2-Aminothiophenes from Methylene-Active Nitriles, Carbonyl Compounds, and Sulfur. Chem. Ber. 1966, 99, 94-100.
    • (1966) Chem. Ber. , vol.99 , pp. 94-100
    • Gewald, K.1    Schinke, E.2    Böttcher, H.3
  • 36
    • 0013474269 scopus 로고
    • The Gewald Synthesis
    • Sabnis, R. W. The Gewald Synthesis. Sulfur Rep. 1994, 16, 1-17.
    • (1994) Sulfur Rep. , vol.16 , pp. 1-17
    • Sabnis, R.W.1
  • 37
    • 0028846473 scopus 로고
    • Preparation of Fused 1,3-Oxazine2,4-diones as Potential Antitumor Agents
    • Player, M. R.; Sowell, J. W. Preparation of Fused 1,3-Oxazine2,4-diones as Potential Antitumor Agents. J. Heterocycl. Chem. 1995, 32, 1537-1540.
    • (1995) J. Heterocycl. Chem. , vol.32 , pp. 1537-1540
    • Player, M.R.1    Sowell, J.W.2
  • 38
  • 39
    • 84988134467 scopus 로고
    • The Facile Synthesis of 2-Aminothieno[2,3-d][l,3]thiazin-4-ones, in Some Cases 5,6-Anellated
    • Leistner, S.; Gütschow, M. Wagner, G. The Facile Synthesis of 2-Aminothieno[2,3-d][l,3]thiazin-4-ones, in Some Cases 5,6-Anellated. Synthesis 1987, 466-470.
    • (1987) Synthesis , pp. 466-470
    • Leistner, S.1    Gütschow, M.2    Wagner, G.3
  • 40
    • 0001396685 scopus 로고
    • The Slow-Binding and Slow, Tight-Binding Inhibition of Enzyme-Catalyzed Reactions
    • Morrison, J. F. The Slow-Binding and Slow, Tight-Binding Inhibition of Enzyme-Catalyzed Reactions. Trends Biochem. Sci. 1982,7, 102-105.
    • (1982) Trends Biochem. Sci. , vol.7 , pp. 102-105
    • Morrison, J.F.1
  • 41
    • 0007729819 scopus 로고
    • Hydrolysis and Mechanism of Diaryldithiocarbamates in 20% Aqueous Dioxane
    • Mindl, J.; Sulzer, J.; Vecera, M. Hydrolysis and Mechanism of Diaryldithiocarbamates in 20% Aqueous Dioxane. Collect. Czech. Chem. Commun. 1981, 46, 1970-1975.
    • (1981) Collect. Czech. Chem. Commun. , vol.46 , pp. 1970-1975
    • Mindl, J.1    Sulzer, J.2    Vecera, M.3
  • 42
    • 14444285685 scopus 로고
    • Kinetics and Mechanism of Hydrolysis of Benzhydryl N-Arylthiocarbamates and Study of their IR Spectra
    • Mindl, J.; Sterba, V.; Kaderabek, V.; Klicnar, J. Kinetics and Mechanism of Hydrolysis of Benzhydryl N-Arylthiocarbamates and Study of their IR Spectra. Collect. Czech. Chem. Commun. 1984, 49, 1577-1591.
    • (1984) Collect. Czech. Chem. Commun. , vol.49 , pp. 1577-1591
    • Mindl, J.1    Sterba, V.2    Kaderabek, V.3    Klicnar, J.4
  • 43
    • 0025265667 scopus 로고
    • Reaction of Porcine Elastase with 7-Substituted 3-Alkoxy-4-chloroisocoumarins: Design of Potent Inhibitors Using the Crystal Structure of the Complex Formed with 4-Chloro-3-ethoxy-7-guanidinoisocoumarin
    • Powers, J. C.; Oleksyszyn, J.; Narasimhan, S. L.; Kam, C.-M.; Radhakrishnan, R.; Meyer, E. F. Reaction of Porcine Elastase with 7-Substituted 3-Alkoxy-4-chloroisocoumarins: Design of Potent Inhibitors Using the Crystal Structure of the Complex Formed with 4-Chloro-3-ethoxy-7-guanidinoisocoumarin. Biochemistry 1990, 29, 3108-3118.
    • (1990) Biochemistry , vol.29 , pp. 3108-3118
    • Powers, J.C.1    Oleksyszyn, J.2    Narasimhan, S.L.3    Kam, C.-M.4    Radhakrishnan, R.5    Meyer, E.F.6
  • 44
    • 0004965834 scopus 로고
    • Heterocyclic β-Enamino Esters, Versatile Synthons in Heterocyclic Synthesis
    • Katritzky, A. R., Ed.; Academic Press: San Diego
    • Wamhoff, H. Heterocyclic β-Enamino Esters, Versatile Synthons in Heterocyclic Synthesis. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1985; Vol. 38, pp 299-368.
    • (1985) Advances in Heterocyclic Chemistry , vol.38 , pp. 299-368
    • Wamhoff, H.1
  • 45
    • 0028327744 scopus 로고
    • L,3-Oxazino[4,5-b]indole-2,4-(lH,9H)-diones and 5,6-Dimethylpyrrolo[2,3-d]-l,3-oxazin-2,4-(lH,7H)-diones as Serine Protease Inhibitors
    • Player, M. R.; Sowell, J. W.; Patil, G. S.; Kam, C.-M.; Powers, J. C. l,3-Oxazino[4,5-b]indole-2,4-(lH,9H)-diones and 5,6-Dimethylpyrrolo[2,3-d]-l,3-oxazin-2,4-(lH,7H)-diones as Serine Protease Inhibitors. Bioorg. Med. Chem. Lett. 1994, 4, 949-954.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 949-954
    • Player, M.R.1    Sowell, J.W.2    Patil, G.S.3    Kam, C.-M.4    Powers, J.C.5
  • 47
    • 0020121233 scopus 로고
    • Convenient Purification of Human Spleen Fibrinolytic Proteinase and Human Leucocyte Elastase by Affinity Chromatography
    • Okada, Y.; Tsuda, Y.; Nagamatsu, Y.; Okamoto, U. Convenient Purification of Human Spleen Fibrinolytic Proteinase and Human Leucocyte Elastase by Affinity Chromatography. Chem. Pharm. Bull. 1982, 30, 1528-1530.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 1528-1530
    • Okada, Y.1    Tsuda, Y.2    Nagamatsu, Y.3    Okamoto, U.4
  • 48
    • 0343251340 scopus 로고
    • Synthesis of 2-Cyano-2-alkylethanols and their Resultion through Gas-liquid Chromatography
    • Prepared from 3-methyl-2-butanone and te/t-butyl cyanoacetate according to: Julia, S.; Torrent, J.; Olle, J.; Ramio, J.; Sanz, M. Synthesis of 2-Cyano-2-alkylethanols and their Resultion through Gas-liquid Chromatography. Afinidad 1974, 31, 117-123.
    • (1974) Afinidad , vol.31 , pp. 117-123
    • Julia, S.1    Torrent, J.2    Olle, J.3    Ramio, J.4    Sanz, M.5
  • 49
    • 14444269441 scopus 로고    scopus 로고
    • Unpublished results
    • Prepared from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3carboxylic acid and thiophosgene: Leistner, S. Unpublished results.
    • Leistner, S.1
  • 50
    • 0020611596 scopus 로고
    • The Synthesis of 2,3,4,5Tetrahydroimidazo[l,2-6]quinazolin-2,5-diones and Analogous 2,3,4,5-Tetrahydroimidazo[l,2-a]thieno[2,3-d] (or [3,2-d])-pyrimidin-2,5-diones
    • Kienzle, F.; Kaiser, A.; Minder, R. E. The Synthesis of 2,3,4,5Tetrahydroimidazo[l,2-6]quinazolin-2,5-diones and Analogous 2,3,4,5-Tetrahydroimidazo[l,2-a]thieno[2,3-d] (or [3,2-d])-pyrimidin-2,5-diones. Helv. Chim. Acta 1983, 66, 148-157.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 148-157
    • Kienzle, F.1    Kaiser, A.2    Minder, R.E.3


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