메뉴 건너뛰기




Volumn 37, Issue 26, 1994, Pages 4538-4553

Inhibition of Human Neutrophil Elastase with Peptidyl Electrophilic Ketones. 2. Orally Active PG-Val-Pro-Val Pentafluoroethyl Ketones

Author keywords

[No Author keywords available]

Indexed keywords

ELASTASE; KETONE; LEUKOCYTE ENZYME; MDL 101146; MDL 103139; MDL 103542; N [4 (MORPHOLINOCARBONYL)BENZOYL]VALYL N [3,3,4,4,4 PENTAFLUORO 1 ISOPROPYL 2 OXOBUTYL]PROLINAMIDE; UNCLASSIFIED DRUG;

EID: 0028569229     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00052a013     Document Type: Article
Times cited : (54)

References (50)
  • 1
    • 0004413964 scopus 로고
    • Pulmonary Emphysema, the Rationale for Intervention
    • Krell, R. D.; Giles, R. E. Pulmonary Emphysema, the Rationale for Intervention. Ann. N. Y. Acad. Sci. 1991, 624, 1-370
    • (1991) Ann. N. Y. Acad. Sci. , vol.624 , pp. 1-370
    • Krell, R.D.1    Giles, R.E.2
  • 3
    • 0021919760 scopus 로고
    • Elastase and Emphysema
    • Current Assessment of the Protease-Antiprotease Hypothesis.
    • Janoff, A. Elastase and Emphysema. Current Assessment of the Protease-Antiprotease Hypothesis. Am. Rev. Respir. Dis. 1985, 132, 417-433
    • (1985) Am. Rev. Respir. Dis. , vol.132 , pp. 417-433
    • Janoff, A.1
  • 4
    • 0021298375 scopus 로고
    • Interactions of Granulocyte Proteases with Inhibitors in Rheumatoid-Arthritis
    • Ekerot, L.; Ohlsson, K. Interactions of Granulocyte Proteases with Inhibitors in Rheumatoid-Arthritis. Adv. Exp. Med. Biol. 1984, 167, 335-344
    • (1984) Adv. Exp. Med. Biol. , vol.167 , pp. 335-344
    • Ekerot, L.1    Ohlsson, K.2
  • 5
    • 24444434861 scopus 로고
    • Advances in Inflammation Research
    • Ottemess, I., et al., Eds.; Raven Press: New York
    • Bonney, R. J.; Smith, R. J. In Advances in Inflammation Research; Ottemess, I., et al., Eds.; Raven Press: New York, 1986; Vol. II
    • (1986) , vol.2
    • Bonney, R.J.1    Smith, R.J.2
  • 7
    • 0021339660 scopus 로고
    • Granulocyte Neutral Proteases and Pseudomonas Elastase as Possible Causes of Airway Damage in Patients with Cystic Fibrosis
    • Suter, S.; Schaad, L.; Roux, L.; Nydegger, V. E.; Waldvogel, F. A. Granulocyte Neutral Proteases and Pseudomonas Elastase as Possible Causes of Airway Damage in Patients with Cystic Fibrosis. J. Infect. Dis. 1984, 149, 523-531.
    • (1984) J. Infect. Dis. , vol.149 , pp. 523-531
    • Suter, S.1    Schaad, L.2    Roux, L.3    Nydegger, V.E.4    Waldvogel, F.A.5
  • 8
    • 0021318932 scopus 로고
    • Sputum Soluble Phase Proteins and Elastase Activity in Patients with Cystic Fibrosis
    • Jackson, A. H.; Hill, S. L.; Afford, S. C.; Stockley, R. A. Sputum Soluble Phase Proteins and Elastase Activity in Patients with Cystic Fibrosis. J. Respir. Dis. 1984, 65, 119-124
    • (1984) J. Respir. Dis. , vol.65 , pp. 119-124
    • Jackson, A.H.1    Hill, S.L.2    Afford, S.C.3    Stockley, R.A.4
  • 10
    • 0019301316 scopus 로고
    • On the Pathogenesis of Glomerulonephritis: a Clinico-Pathological Study Indicating That Neutrophils Attack and Degrade Glomerular Basement Membrane
    • Sanders, E.; Davies, M.; Coles, A. On the Pathogenesis of Glomerulonephritis: a Clinico-Pathological Study Indicating That Neutrophils Attack and Degrade Glomerular Basement Membrane. Renal Physiol. 1980, 3, 355-359
    • (1980) Renal Physiol. , vol.3 , pp. 355-359
    • Sanders, E.1    Davies, M.2    Coles, A.3
  • 11
    • 0025176920 scopus 로고
    • Synthesis of Peptidyl Fluoromethyl Ketones and Peptidyl α-Keto Esters as Inhibitors of Porcine Pancreatic Elastase, Human Neutrophil Elastase, and Rat and Human Cathepsin G
    • Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. Synthesis of Peptidyl Fluoromethyl Ketones and Peptidyl α-Keto Esters as Inhibitors of Porcine Pancreatic Elastase, Human Neutrophil Elastase, and Rat and Human Cathepsin G. J. Med. Chem. 1990, 33, 394-407
    • (1990) J. Med. Chem. , vol.33 , pp. 394-407
    • Peet, N.P.1    Burkhart, J.P.2    Angelastro, M.R.3    Giroux, E.L.4    Mehdi, S.5    Bey, P.6    Kolb, M.7    Neises, B.8    Schirlin, D.9
  • 14
    • 0027484224 scopus 로고
    • Synthetic and Naturally Occurring Protease Inhibitors Containing an Electrophilic Carbonyl Group
    • Mehdi, S. Synthetic and Naturally Occurring Protease Inhibitors Containing an Electrophilic Carbonyl Group. Bioorg. Chem. 1993, 21, 249-259
    • (1993) Bioorg. Chem. , vol.21 , pp. 249-259
    • Mehdi, S.1
  • 15
    • 0026648075 scopus 로고
    • Efficient Preparation of Peptidyl Pentafluoroethyl Ketones
    • Angelastro, M. R.; Burkhart, J. P.; Bey, P.; Peet, N. P. Efficient Preparation of Peptidyl Pentafluoroethyl Ketones. Tetrahedron Lett. 1992, 33, 3265-3268
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3265-3268
    • Angelastro, M.R.1    Burkhart, J.P.2    Bey, P.3    Peet, N.P.4
  • 17
    • 33845184924 scopus 로고
    • An Efficient Synthesis of Novel α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides
    • Angelastro, M. R.; Peet, N. P.; Bey, P. An Efficient Synthesis of Novel α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides. J. Org. Chem. 1989, 54, 3913-3916
    • (1989) J. Org. Chem. , vol.54 , pp. 3913-3916
    • Angelastro, M.R.1    Peet, N.P.2    Bey, P.3
  • 18
    • 0025058702 scopus 로고
    • α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides as Novel Inhibitors of Cysteine and Serine Proteinases
    • Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides as Novel Inhibitors of Cysteine and Serine Proteinases. J. Med. Chem. 1990, 33, 11-13
    • (1990) J. Med. Chem. , vol.33 , pp. 11-13
    • Angelastro, M.R.1    Mehdi, S.2    Burkhart, J.P.3    Peet, N.P.4    Bey, P.5
  • 19
    • 0025241833 scopus 로고
    • A Novel Method for the Preparation of Peptidyl α-Keto Esters
    • Burkhart, J. P.; Peet, N. P.; Bey, P. A Novel Method for the Preparation of Peptidyl α-Keto Esters. Tetrahedron Lett. 1990, 31, 1385-1388
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1385-1388
    • Burkhart, J.P.1    Peet, N.P.2    Bey, P.3
  • 20
    • 0025963466 scopus 로고
    • Preparation of Trifluoromethyl Ketones and Related Fluorinated Ketones
    • Begue, J.-P.; Bonnet-Delpon, D. Preparation of Trifluoromethyl Ketones and Related Fluorinated Ketones. Tetrahedron 1991, 47, 3207-3258
    • (1991) Tetrahedron , vol.47 , pp. 3207-3258
    • Begue, J.-P.1    Bonnet-Delpon, D.2
  • 21
    • 0025021432 scopus 로고
    • The Synthesis of Arginylfluoroalkanes, Their Inhibition of Trypsin and Blood-Coagulation Serine Proteinases and Their Anticoagulant Activity
    • Ueda, T.; Kam, C.-M.; Powers, J. C. The Synthesis of Arginylfluoroalkanes, Their Inhibition of Trypsin and Blood-Coagulation Serine Proteinases and Their Anticoagulant Activity. Biochem. J. 1990, 265, 539-545
    • (1990) Biochem. J. , vol.265 , pp. 539-545
    • Ueda, T.1    Kam, C.-M.2    Powers, J.C.3
  • 23
    • 27844466269 scopus 로고
    • N-Methoxy-N-Methylamides as Effective Acylating Agents
    • Nahm, S.; Weinreb, S. M. N-Methoxy-N-Methylamides as Effective Acylating Agents. Tetrahedron Lett. 1981, 22, 3815-3818
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 24
    • 85004872164 scopus 로고
    • An Efficient Synthesis of Optically Active α-(t-Butoxycarbonylamino)aldehydes from α-Amino Acids
    • Fehrentz, J.-A.; Castro, B. An Efficient Synthesis of Optically Active α-(t-Butoxycarbonylamino)aldehydes from α-Amino Acids. Synthesis 1983, 676-678
    • (1983) Synthesis , pp. 676-678
    • Fehrentz, J.-A.1    Castro, B.2
  • 25
    • 0001522346 scopus 로고
    • Nucleophilic Addition of the Pentafluoroethyl Group to Aldehydes, Ketones, and Esters
    • Gassman, P. G.; O'Reilly, N. J. Nucleophilic Addition of the Pentafluoroethyl Group to Aldehydes, Ketones, and Esters. J. Org. Chem. 1987, 52, 2481-2490
    • (1987) J. Org. Chem. , vol.52 , pp. 2481-2490
    • Gassman, P.G.1    O'Reilly, N.J.2
  • 26
    • 0022844081 scopus 로고
    • The Synthesis of Benzindene Prostacyclin Analogs as Potential Antiulcer Agents
    • Alexander, D. L.; Lin, C. H. The Synthesis of Benzindene Prostacyclin Analogs as Potential Antiulcer Agents. Prostaglandins 1986, 32, 647-653
    • (1986) Prostaglandins , vol.32 , pp. 647-653
    • Alexander, D.L.1    Lin, C.H.2
  • 27
  • 28
    • 85068705507 scopus 로고
    • Esterification and Alkylation Reactions Employing Isoureas
    • Mathias, L. J. Esterification and Alkylation Reactions Employing Isoureas. Synthesis 1979, 561-576
    • (1979) Synthesis , pp. 561-576
    • Mathias, L.J.1
  • 29
    • 84989478646 scopus 로고
    • Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis
    • Mancuso, A. J.; Swern, D. Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis. Synthesis 1981, 165-184
    • (1981) Synthesis , pp. 165-184
    • Mancuso, A.J.1    Swern, D.2
  • 31
    • 85022409124 scopus 로고
    • A Simple Technique for Endotracheal Instillation of Drugs in the Rat
    • Schranfnagel, D.; Harshbarger, R.; Treviranus, K. A Simple Technique for Endotracheal Instillation of Drugs in the Rat. Am. Rev. Respir. Dis. 1984, 129, A234
    • (1984) Am. Rev. Respir. Dis. , vol.129 , pp. A234
    • Schranfnagel, D.1    Harshbarger, R.2    Treviranus, K.3
  • 32
    • 0003494840 scopus 로고
    • 17th ed.; Todd, Sanford, Davidsohn, Eds.; W. B. Saunders Co.: Philadelphia, PA
    • Henry, J. B. In Clinical Diagnosis and Management by Laboratory Methods, 17th ed.; Todd, Sanford, Davidsohn, Eds.; W. B. Saunders Co.: Philadelphia, PA, 1984; pp 580-583
    • (1984) Clinical Diagnosis and Management by Laboratory Methods , pp. 580-583
    • Henry, J.B.1
  • 34
    • 0025343238 scopus 로고
    • A Comparison of ai-Proteinase Inhibitor Methoxy-succinyl-Ala-Ala-Pro-Val-Chloromethylketone and Specific β-Lactam Inhibitors in an Acute Model of Human Polymorphonuclear Leukocyte Elastase-induced Lung Hemorrhage in the Hamster
    • Fletcher, D. S.; Osinga, D. G.; Hand, K. M.; Dellea, P. S.; Ashe, B. M.; Mumford, R. A.; Davies, P.; Hagmann, W.; Finke, P. E.; Doherty, J. B.; Bonney, R. J. A Comparison of ai-Proteinase Inhibitor Methoxy-succinyl-Ala-Ala-Pro-Val-Chloromethylketone and Specific β-Lactam Inhibitors in an Acute Model of Human Polymorphonuclear Leukocyte Elastase-induced Lung Hemorrhage in the Hamster. Am. Rev. Respir. Dis. 1990, 141, 672- 677
    • (1990) Am. Rev. Respir. Dis. , vol.141 , pp. 672-677
    • Fletcher, D.S.1    Osinga, D.G.2    Hand, K.M.3    Dellea, P.S.4    Ashe, B.M.5    Mumford, R.A.6    Davies, P.7    Hagmann, W.8    Finke, P.E.9    Doherty, J.B.10    Bonney, R.J.11
  • 37
    • 0028365927 scopus 로고
    • Pharmacology of N-[4-(4-Morpholinylcarbonyl)benzoyl]-L-valyl-N-[3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl]-L-prolinamide (MDL 101,146); A Potent Orally Active Inhibitor of Human Neutrophil Elastase
    • Durham, S. L.; Hare, C. M.; Angelastro, M. R.; Burkhart, J. P.; Koehl, J. R.; Marquart, A. L.; Mehdi, S.; Peet, N. P.; Janusz, M. J. Pharmacology of N-[4-(4-Morpholinylcarbonyl)benzoyl]-L-valyl-N-[3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl]-L-prolinamide (MDL 101,146); A Potent Orally Active Inhibitor of Human Neutrophil Elastase. J. Pharmacol. Exp. Ther. 1994, 270, 185-191
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 185-191
    • Durham, S.L.1    Hare, C.M.2    Angelastro, M.R.3    Burkhart, J.P.4    Koehl, J.R.5    Marquart, A.L.6    Mehdi, S.7    Peet, N.P.8    Janusz, M.J.9
  • 39
    • 0027535899 scopus 로고
    • Studies Directed Toward the Design of Orally Active Renin Inhibitors
    • Development of the Efficacious, Bioavailable Renin Inhibitor (2S)-2-Benzyl-3-[[(1-methylpiperazine-4-yl)sulfonyl]propionyl]-3-thiazol-4-yl-L-alanine Amide of (2S,3R,4S)-2-Amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (A-72517).
    • Rosenberg, S. H.; Spina, K. P.; Condon, S. L.; Palakowski, J.; Yao, Z.; Kovar, P.; Stein, H. H.; Cohen, J.; Barlow, J. L.; Klinghofer, V.; Egan, D. A.; Tricarico, K. A.; Perun, T. J.; Baker, W. R.; Kleinert, H. D. Studies Directed Toward the Design of Orally Active Renin Inhibitors. 2. Development of the Efficacious, Bioavailable Renin Inhibitor (2S)-2-Benzyl-3-[[(1-methylpiperazine-4-yl)sulfonyl]propionyl]-3-thiazol-4-yl-L-alanine Amide of (2S,3R,4S)-2-Amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (A-72517). J. Med. Chem. 1993, 36, 460-467
    • (1993) J. Med. Chem. , vol.36 , Issue.2 , pp. 460-467
    • Rosenberg, S.H.1    Spina, K.P.2    Condon, S.L.3    Palakowski, J.4    Yao, Z.5    Kovar, P.6    Stein, H.H.7    Cohen, J.8    Barlow, J.L.9    Klinghofer, V.10    Egan, D.A.11    Tricarico, K.A.12    Perun, T.J.13    Baker, W.R.14    Kleinert, H.D.15
  • 41
    • 0025743702 scopus 로고
    • Influence of Mobile Phase Composition on Evaluation of Lipophilicity of Partition Chromatography
    • Kuchar, M.; Kraus, E.; Jelinkova, M. Influence of Mobile Phase Composition on Evaluation of Lipophilicity of Partition Chromatography. J. Chromatogr. 1991, 557, 399-411
    • (1991) J. Chromatogr. , vol.557 , pp. 399-411
    • Kuchar, M.1    Kraus, E.2    Jelinkova, M.3
  • 42
    • 0000081181 scopus 로고
    • Measurement of Lipophilicity by High-Performance Liquid Chromatography
    • Comparison with Calculated Lipophilicity Values.
    • Sabatka, J. J.; Minick, D. J.; Shumaker, T. K.; Hodgson, G. L.; Brent, D. A. Measurement of Lipophilicity by High-Performance Liquid Chromatography. Comparison with Calculated Lipophilicity Values. J. Chromatogr. 1987, 384, 349-356
    • (1987) J. Chromatogr. , vol.384 , pp. 349-356
    • Sabatka, J.J.1    Minick, D.J.2    Shumaker, T.K.3    Hodgson, G.L.4    Brent, D.A.5
  • 43
    • 0023017975 scopus 로고
    • Determination of Hydrophobic Parameters by Reversed-Phase Liquid Chromatography: Theory, Experimental Techniques, and Application in Studies on Quantitative Structure-Activity Relationships
    • Braumann, T. Determination of Hydrophobic Parameters by Reversed-Phase Liquid Chromatography: Theory, Experimental Techniques, and Application in Studies on Quantitative Structure-Activity Relationships. J. Chromatogr. 1986, 373, 191-225
    • (1986) J. Chromatogr. , vol.373 , pp. 191-225
    • Braumann, T.1
  • 44
    • 0018637936 scopus 로고
    • Correlation of Biological Activity and High-Pressure Liquid Chromatographic Retention Index for a Series of Propanolol, Barbiturate, and Anthranilic Acid Analogues
    • Baker, J. K.; Rauls, D. O.; Borne, R. F. Correlation of Biological Activity and High-Pressure Liquid Chromatographic Retention Index for a Series of Propanolol, Barbiturate, and Anthranilic Acid Analogues. J. Med. Chem. 1979, 22, 1301-1306
    • (1979) J. Med. Chem. , vol.22 , pp. 1301-1306
    • Baker, J.K.1    Rauls, D.O.2    Borne, R.F.3
  • 45
    • 0000856541 scopus 로고
    • Entropy, Enthalpy, and Side Arm Porphyrins
    • Thermodynamics of Axial Ligand Competition Between 3-Picoline and a Series of 3-Pyridyl Ligands Covalently Attached to Zinc Tetraphenylporphyrin.
    • Walker, F. A.; Benson, M. Entropy, Enthalpy, and Side Arm Porphyrins. 1. Thermodynamics of Axial Ligand Competition Between 3-Picoline and a Series of 3-Pyridyl Ligands Covalently Attached to Zinc Tetraphenylporphyrin. J. Am. Chem. Soc. 1980, 102, 5530-5538
    • (1980) J. Am. Chem. Soc. , vol.102 , Issue.1 , pp. 5530-5538
    • Walker, F.A.1    Benson, M.2
  • 46
    • 8944225096 scopus 로고
    • Analgesics
    • Basic Amides of α-Alkoxydiphenylacetic Acids.
    • Krapcho, J.; Turk, C. F. Analgesics. Basic Amides of α-Alkoxydiphenylacetic Acids. J. Med. Chem. 1963, 6, 547-550
    • (1963) J. Med. Chem. , vol.6 , pp. 547-550
    • Krapcho, J.1    Turk, C.F.2
  • 47
    • 0007278042 scopus 로고
    • An Improved Synthesis of Benzoyl Acetates
    • Buckle, D. R.; Smith, H. An Improved Synthesis of Benzoyl Acetates. J. Chem. Soc. C 1971, 2821-2823
    • (1971) J. Chem. Soc. C , pp. 2821-2823
    • Buckle, D.R.1    Smith, H.2
  • 49
    • 0025804212 scopus 로고
    • An Improved Acid Chloride Preparation via Phase Transfer Catalysis
    • Burdett, K. A. An Improved Acid Chloride Preparation via Phase Transfer Catalysis. Synthesis 1991, 441-442
    • (1991) Synthesis , pp. 441-442
    • Burdett, K.A.1
  • 50
    • 84979194192 scopus 로고
    • Syntheses in the Pyran Series
    • Braun, J. V.; Köhler, Z. Syntheses in the Pyran Series. Chem. Ber. 1917, 50, 1657-1658
    • (1917) Chem. Ber. , vol.50 , pp. 1657-1658
    • Braun, J.V.1    Köhler, Z.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.