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Volumn 36, Issue 17, 1993, Pages 2431-2447

Activated Ketone Based Inhibitors of Human Renin

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBONYL DERIVATIVE; KETONE DERIVATIVE; RENIN; RENIN INHIBITOR;

EID: 0027172371     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00069a001     Document Type: Article
Times cited : (93)

References (63)
  • 1
    • 0020321280 scopus 로고
    • Angiotensin-Converting Enzyme Inhibitors: Medicinal Chemistry and Biological Actions
    • Petrillo, E. W., Jr.; Ondetti, M. A. Angiotensin-Converting Enzyme Inhibitors: Medicinal Chemistry and Biological Actions. Med. Res. Rev. 1982, 2, 1–38.
    • (1982) Med. Res. Rev. , vol.2 , pp. 1-38
    • Petrillo, E.W.1    Ondetti, M.A.2
  • 2
    • 0025360877 scopus 로고
    • Renin Inhibitors
    • For a review of early work on renin inhibitors, see
    • For a review of early work on renin inhibitors, see:Greenlee, W. J. Renin Inhibitors. Med. Res. Rev. 1990, 10, 173–226.
    • (1990) Med. Res. Rev. , vol.10 , pp. 173-226
    • Greenlee, W.J.1
  • 7
    • 0003723604 scopus 로고
    • Research monographs in cell and tissue physiology; Dingle, J. T., Gordon, J. L., General Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands
    • Barrett, A. J.; Salvesen, G. Eds. Proteinase Inhibitors; Research monographs in cell and tissue physiology; Dingle, J. T., Gordon, J. L., General Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1986.
    • (1986) Proteinase Inhibitors
    • Barrett, A.J.1    Salvesen, G.2
  • 8
    • 0021832534 scopus 로고
    • Fluoro Retone Inhibitors of Hydrolytic Enzymes
    • Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Fluoro Retone Inhibitors of Hydrolytic Enzymes. Biochemistry 1985, 24, 1813–1817.
    • (1985) Biochemistry , vol.24 , pp. 1813-1817
    • Gelb, M.H.1    Svaren, J.P.2    Abeles, R.H.3
  • 10
    • 2142652751 scopus 로고
    • Renin Inhibitors. Dipeptide Analogues of Angiotensinogen Incorporating Transition-State, Nonpeptidic Replacements at the Scissile Bond
    • Bolis, G.; Fung, A. R. L.; Greer, J.; Kleinert, H. D.; Marcotte, P. A.; Perun, T. J.; Plattner, J. J.; Stein, H. H. Renin Inhibitors. Dipeptide Analogues of Angiotensinogen Incorporating Transition-State, Nonpeptidic Replacements at the Scissile Bond. J. Med. Chem. 1987, 30, 1729–1737.
    • (1987) J. Med. Chem. , vol.30 , pp. 1729-1737
    • Bolis, G.1    Fung, A.R.L.2    Greer, J.3    Kleinert, H.D.4    Marcotte, P.A.5    Perun, T.J.6    Plattner, J.J.7    Stein, H.H.8
  • 11
    • 0023550081 scopus 로고
    • Renin Inhibitors Based on Novel Dipeptide Analogues. Incorporation of the Dehydrohydroxyethylene Isostere at the Scissile Bond
    • Rempf, D. J.; Lara, E.; Stein, H. H.; Cohen, J.; Plattner, J. J. Renin Inhibitors Based on Novel Dipeptide Analogues. Incorporation of the Dehydrohydroxyethylene Isostere at the Scissile Bond. J. Med. Chem. 1987, 30, 1978–1983.
    • (1987) J. Med. Chem. , vol.30 , pp. 1978-1983
    • Rempf, D.J.1    Lara, E.2    Stein, H.H.3    Cohen, J.4    Plattner, J.J.5
  • 12
    • 0023553458 scopus 로고
    • Optimization and In Vivo Evaluations of a Series of Small, Potent, and Specific Renin Inhibitors Containing a Novel Leu-Val Replacement
    • Dellaria, J. F.; Maki, R. G.; Bopp, B. A.; Cohen, J.; Kleinert, H. D.; Luly, J. R.; Merits, L; Plattner, J. J.; Stein, H. H. Optimization and In Vivo Evaluations of a Series of Small, Potent, and Specific Renin Inhibitors Containing a Novel Leu-Val Replacement. J. Med. Chem. 1987, 30, 2137–2144.
    • (1987) J. Med. Chem. , vol.30 , pp. 2137-2144
    • Dellaria, J.F.1    Maki, R.G.2    Bopp, B.A.3    Cohen, J.4    Kleinert, H.D.5    Luly, J.R.6    Merits, L.7    Plattner, J.J.8    Stein, H.H.9
  • 14
    • 85004872164 scopus 로고    scopus 로고
    • An Efficient Synthesis of Optically Active-α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids
    • The Weinreb amide 1 is extremely stable and can be safely stored at room temperature. The procedure for preparing aldehyde 2 via the stable Weinreb amide was developed by Dr. Harold Weiler. For similar synthesis of various α-amino aldehydes, see
    • The Weinreb amide 1 is extremely stable and can be safely stored at room temperature. The procedure for preparing aldehyde 2 via the stable Weinreb amide was developed by Dr. Harold Weiler. For similar synthesis of various α-amino aldehydes, see: (a)Fehrentz, J.-A.; Castro, B. An Efficient Synthesis of Optically Active-α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids. Synthesis 1983, 676–678
    • Synthesis , vol.1983 , pp. 676-678
    • Fehrentz, J.-A.1    Castro, B.2
  • 15
    • 84988080855 scopus 로고    scopus 로고
    • A Convenient and Versatile Synthesis of Chiral Aliphatic and Allylic Amines
    • Saari, W. S.; Fisher, T. E. A Convenient and Versatile Synthesis of Chiral Aliphatic and Allylic Amines. Synthesis 1990, 453–454
    • Synthesis , vol.1990 , pp. 453-454
    • Saari, W.S.1    Fisher, T.E.2
  • 18
    • 4344664124 scopus 로고
    • Configurational Stability of N-Protected α-Amino Aldehydes
    • For preparation of configurationaly stable N-protected α-amino aldehydes
    • For preparation of configurationaly stable N-protected α-amino aldehydes, see:Lubell, W. D.; Rapoport, H. Configurational Stability of N-Protected α-Amino Aldehydes. J. Am. Chem. Soc. 1987, 109, 236–239.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 236-239
    • Lubell, W.D.1    Rapoport, H.2
  • 19
    • 0023686354 scopus 로고
    • Peptidic Trifluoromethyl Alcohols and Ketones. A General Synthesis and Application as Renin Inhibitors
    • For a preliminary communication on the preparation of fluoro ketone 11, see
    • For a preliminary communication on the preparation of fluoro ketone 11, see:Patel, D. V.; Rielly-Gauvin, K.; Ryono, Denis, E. Peptidic Trifluoromethyl Alcohols and Ketones. A General Synthesis and Application as Renin Inhibitors. Tetrahedron Lett. 1988, 29, 4665–4668.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4665-4668
    • Patel, D.V.1    Rielly-Gauvin, K.2    Ryono3    Denis, E.4
  • 20
    • 0001553083 scopus 로고
    • A Versatile Synthesis of Peptidyl Fluoromethyl Ketones
    • Imperiali, B.; Abeles, R. H. A Versatile Synthesis of Peptidyl Fluoromethyl Ketones. Tetrahedron Lett. 1986, 27, 135–138.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 135-138
    • Imperiali, B.1    Abeles, R.H.2
  • 21
    • 34447110909 scopus 로고
    • Inhibition of Human Leukocyte Elastase by Peptide Trifluoromethyl Ketones
    • 193rd National Meeting of the American Chemical Society, Denver, Colorado, April 5–10, 1987; American Chemical Society: Washington DC, MEDI 0001
    • Bergeson, S. H.; Edwards, P. D.; Krell, R. D.; Shaw, A.; Stein, R. L.; Stein, M. M.; Strimpler, A. M.; Trainor, D. A.; Wildonger, R. A.; Wolanin, D. J. Inhibition of Human Leukocyte Elastase by Peptide Trifluoromethyl Ketones. In Abstracts of Papers; 193rd National Meeting of the American Chemical Society, Denver, Colorado, April 5–10, 1987; American Chemical Society: Washington DC, 1987; MEDI 0001.
    • (1987) Abstracts of Papers
    • Bergeson, S.H.1    Edwards, P.D.2    Krell, R.D.3    Shaw, A.4    Stein, R.L.5    Stein, M.M.6    Strimpler, A.M.7    Trainor, D.A.8    Wildonger, R.A.9    Wolanin, D.J.10
  • 23
    • 0015520853 scopus 로고
    • Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis
    • Shioiri, T.; Ninomiya, K.; Yamada, S-I. Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis. J. Am. Chem. Soc. 1972, 94, 6203–6205.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6203-6205
    • Shioiri, T.1    Ninomiya, K.2    Yamada, S.-I.3
  • 24
    • 33644528891 scopus 로고
    • 1 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones
    • 1 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones. J. Org. Chem. 1983, 48, 4155–4156.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
    • Dess, D.B.1    Martin, J.C.2
  • 25
    • 0003102571 scopus 로고
    • An Efficient Procedure for the Oxidation of Fluorinated Carbinols
    • Dess-Martin oxidation is one of the best methods available for oxidation of alcohols bearing electron-deficient groups to the corresponding activated ketones. For the first application of this reagent toward the preparation of trifluoromethyl ketones, see, For a detailed account, see
    • Dess-Martin oxidation is one of the best methods available for oxidation of alcohols bearing electron-deficient groups to the corresponding activated ketones. For the first application of this reagent toward the preparation of trifluoromethyl ketones, see: (a)Linderman, R. J.; Graves, D. M. An Efficient Procedure for the Oxidation of Fluorinated Carbinols. Tetrahedron Lett. 1987, 28, 4259–4262. For a detailed account, see
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4259-4262
    • Linderman, R.J.1    Graves, D.M.2
  • 26
    • 33845183452 scopus 로고
    • Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent
    • Linderman, R. J.; Graves, D. M. Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent. J. Org. Chem. 1989, 54, 661–668.
    • (1989) J. Org. Chem. , vol.54 , pp. 661-668
    • Linderman, R.J.1    Graves, D.M.2
  • 27
    • 37049097212 scopus 로고
    • Bicyclic Heterocycles with Nitrogen at the Ring Junction
    • Application of the Dakin-West Reaction to the Synthesis of Imidazo-[5,1-f]-1,2,4-[triazin-4(3H)-ones
    • Charles, I.; Latham, D. W. S.; Hartley, D.; Oxford, A. W.; Scopes, D. I. C. Bicyclic Heterocycles with Nitrogen at the Ring Junction. Part 2. Application of the Dakin-West Reaction to the Synthesis of Imidazo-[5,1-f]-1,2,4-[triazin-4(3H)-ones. J. Chem. Soc., Perkin Trans. 1, 1980, 1139–1146
    • (1980) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1139-1146
    • Charles, I.1    Latham, D.W.S.2    Hartley, D.3    Oxford, A.W.4    Scopes, D.I.C.5
  • 28
    • 33744576404 scopus 로고
    • Inhibition of Human Leukocyte Elastase, Porcine Pancreatic Elastase and Cathepsin G by Peptide Ketones
    • For one of the first applications of peptidic α-keto esters as protease inhibitors, see, Proceedings of the Ninth American Peptide Symposium; Deber, C. M., Hruby, V. J., Kopple, K. D., Eds.
    • For one of the first applications of peptidic α-keto esters as protease inhibitors, see:Hori, H.; Yasutake, A.; Minematsu, Y.; Powers, J. C. Inhibition of Human Leukocyte Elastase, Porcine Pancreatic Elastase and Cathepsin G by Peptide Ketones. In Peptides Structure and Function; Proceedings of the Ninth American Peptide Symposium; Deber, C. M., Hruby, V. J., Kopple, K. D., Eds.; 1985; pp 819–822.
    • (1985) Peptides Structure and Function , pp. 819-822
    • Hori, H.1    Yasutake, A.2    Minematsu, Y.3    Powers, J.C.4
  • 29
    • 0023910548 scopus 로고
    • New Human Renin Inhibitors Containing an Unnatural Amino Acid, Norstatine
    • Application of α-hydroxy ester based peptides as renin inhibitors was reported right after our own work was completed. See
    • Application of α-hydroxy ester based peptides as renin inhibitors was reported right after our own work was completed. See: (a)Iizuka, K.; Kamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Kiso, Y. New Human Renin Inhibitors Containing an Unnatural Amino Acid, Norstatine. J. Med. Chem. 1988, 31, 701–704.
    • (1988) J. Med. Chem. , vol.31 , pp. 701-704
    • Iizuka, K.1    Kamijo, T.2    Kubota, T.3    Akahane, K.4    Umeyama, H.5    Kiso, Y.6
  • 30
    • 0025050730 scopus 로고
    • Orally Potent Human Renin Inhibitors Derived from Angiotensinogen Transition State: Design, Synthesis, and Mode of Interaction
    • Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y. Orally Potent Human Renin Inhibitors Derived from Angiotensinogen Transition State: Design, Synthesis, and Mode of Interaction. J. Med. Chem. 1990, 33, 2707–2714.
    • (1990) J. Med. Chem. , vol.33 , pp. 2707-2714
    • Iizuka, K.1    Kamijo, T.2    Harada, H.3    Akahane, K.4    Kubota, T.5    Umeyama, H.6    Kiso, Y.7
  • 31
  • 32
    • 0000985286 scopus 로고
    • A General Synthesis of 2-Alkyl Tetronic Acids
    • Damon, R. E.; Luo, T.; Schlessinger, R. H. A General Synthesis of 2-Alkyl Tetronic Acids. Tetrahedron Lett. 1976, 32, 2749–2752.
    • (1976) Tetrahedron Lett. , vol.32 , pp. 2749-2752
    • Damon, R.E.1    Luo, T.2    Schlessinger, R.H.3
  • 33
  • 34
    • 0642318658 scopus 로고
    • New Synthetic Methods from Dithianes. A Convenient Oxidation of Aldehydes to Acids and Esters
    • Ellison, R. A.; Woessner, W. D.; Williams, C. C. New Synthetic Methods from Dithianes. A Convenient Oxidation of Aldehydes to Acids and Esters. J. Org. Chem. 1972, 37, 2757–2759.
    • (1972) J. Org. Chem. , vol.37 , pp. 2757-2759
    • Ellison, R.A.1    Woessner, W.D.2    Williams, C.C.3
  • 35
    • 21944449743 scopus 로고
    • Hydrolysis and Alcoholysis of Orthothio Esters
    • Ellison, R. A.; Woessner, W. D.; Williams, C. C. Hydrolysis and Alcoholysis of Orthothio Esters. J. Org. Chem. 1974, 39, 1430–1433.
    • (1974) J. Org. Chem. , vol.39 , pp. 1430-1433
    • Ellison, R.A.1    Woessner, W.D.2    Williams, C.C.3
  • 36
    • 0000717526 scopus 로고
    • Synthesis of a Model for the BCE Ring System of Bruceantin. A Caveat on the Cyclohexene -> Trans Diaxial Diol Conversion
    • Dailey, O. D., Jr.; Fuchs, P. L. Synthesis of a Model for the BCE Ring System of Bruceantin. A Caveat on the Cyclohexene -> Trans Diaxial Diol Conversion. J. Org. Chem. 1980, 45, 216–236.
    • (1980) J. Org. Chem. , vol.45 , pp. 216-236
    • Dailey, O.D.1    Fuchs, P.L.2
  • 37
    • 0342352714 scopus 로고
    • A General Synthesis of Methyl Aldulosonates Using Tris-(Methylthio) Methyl Lithium as the Ester Anion Equivalent
    • Hengeveld, J. E.; Grief, V.; Tadanier, J.; Lee, C.-M.; Riley, D.; Lartey, P. A. A General Synthesis of Methyl Aldulosonates Using Tris-(Methylthio) Methyl Lithium as the Ester Anion Equivalent. Tetrahedron Lett. 1984, 25, 4075–4078.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4075-4078
    • Hengeveld, J.E.1    Grief, V.2    Tadanier, J.3    Lee, C.-M.4    Riley, D.5    Lartey, P.A.6
  • 38
    • 0018890715 scopus 로고
    • Synthesis of Analogues of the Carboxyl Protease Inhibitor Pepstatin. Effect of Structure on Inhibition of Pepsin and Renin
    • Rich, D. H.; Sun, E. T. O.; Ulm, E. Synthesis of Analogues of the Carboxyl Protease Inhibitor Pepstatin. Effect of Structure on Inhibition of Pepsin and Renin. J. Med. Chem. 1980, 23, 27–33.
    • (1980) J. Med. Chem. , vol.23 , pp. 27-33
    • Rich, D.H.1    Sun, E.T.O.2    Ulm, E.3
  • 40
    • 0000758509 scopus 로고
    • Synthesis of Oxazolidin-2-ones Using Carbonate Ion on a Polymeric Support
    • Cardillo, G.; Orena, M.; Sandri, S.; Tamasini, C. Synthesis of Oxazolidin-2-ones Using Carbonate Ion on a Polymeric Support. Tetrahedron 1985, 41, 163–167.
    • (1985) Tetrahedron , vol.41 , pp. 163-167
    • Cardillo, G.1    Orena, M.2    Sandri, S.3    Tamasini, C.4
  • 41
    • 85022273700 scopus 로고    scopus 로고
    • For preparation of 29, see, US Patent 5,055,466
    • For preparation of 29, see:Weller, H. N. III; Ryono, D. E. US Patent 5,055,466.
    • Weller, H.N.1    Ryono, D.E.2
  • 43
    • 0025241833 scopus 로고
    • A Novel Method for the Preparation of Peptidyl α-Keto Esters
    • A very similar route for preparing peptidyl α-keto esters was reported in the literature after the completion of our own work. See, Their synthesis also lead to an epimeric mixture of α-keto esters; however, racemization in their case was claimed to occur directly during swern oxidation of the chiral α-hydroxy ester intermediate
    • A very similar route for preparing peptidyl α-keto esters was reported in the literature after the completion of our own work. See: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. Their synthesis also lead to an epimeric mixture of α-keto esters; however, racemization in their case was claimed to occur directly during swern oxidation of the chiral α-hydroxy ester intermediate.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1385-1388
    • Burkhart, J.P.1    Peet, N.P.2    Bey, P.3
  • 44
    • 0020477045 scopus 로고
    • Synthesis of 9-(3,4-Dioxopentyl)hypoxanthine, the First Arginine-Directed Purine Derivative: An Irreversible Inactivator for Purine Nucleoside Phosphorylase
    • Salamone, S. J.; Jordan, F. Synthesis of 9-(3,4-Dioxopentyl)hypoxanthine, the First Arginine-Directed Purine Derivative: An Irreversible Inactivator for Purine Nucleoside Phosphorylase. Biochemistry 1982, 21, 6383–6388.
    • (1982) Biochemistry , vol.21 , pp. 6383-6388
    • Salamone, S.J.1    Jordan, F.2
  • 45
    • 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
  • 46
    • 33847801404 scopus 로고
    • Generation and Synthetic Applications of 2-Lithio-1,3-dithianes
    • Seebach, D.; Corey, B. J. Generation and Synthetic Applications of 2-Lithio-1,3-dithianes. J. Org. Chem. 1975, 40, 231–237.
    • (1975) J. Org. Chem. , vol.40 , pp. 231-237
    • Seebach, D.1    Corey, B.J.2
  • 47
    • 75749150674 scopus 로고    scopus 로고
    • Alkylation of 2-Lithio-1,3-dithianes with Arenesulfonates of Primary Alcohols
    • Seebach, D.; Welka, E-M. Alkylation of 2-Lithio-1,3-dithianes with Arenesulfonates of Primary Alcohols. Synthesis 1976, 476–477
    • Synthesis , vol.1976 , pp. 476-477
    • Seebach, D.1    Welka, E.-M.2
  • 48
    • 0037768402 scopus 로고
    • Optically Active N-Protected α-Amino Aldehydes in Organic Synthesis
    • For a review of stereoselective synthesis of β-amino alcohols from α-amino aldehydes, see
    • For a review of stereoselective synthesis of β-amino alcohols from α-amino aldehydes, see:Jurczak, J.; Golebiowski, A. Optically Active N-Protected α-Amino Aldehydes in Organic Synthesis. Chem. Rev. 1989, 89, 149–164.
    • (1989) Chem. Rev. , vol.89 , pp. 149-164
    • Jurczak, J.1    Golebiowski, A.2
  • 49
    • 84985516476 scopus 로고
    • Stereoselective Synthesis of β-Amino Alcohols from Optically Active α-Amino Acids
    • Also see:Reetz, M. T.; Drewes, M. W.; Schmitz, A. Stereoselective Synthesis of β-Amino Alcohols from Optically Active α-Amino Acids. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141–1143.
    • (1987) Angew. Chem., Int. Ed. Engl. , vol.26 , pp. 1141-1143
    • Reetz, M.T.1    Drewes, M.W.2    Schmitz, A.3
  • 51
    • 85065132463 scopus 로고    scopus 로고
    • Ceric Ion Oxidation in Organic Chemistry
    • Ho, T.-K. Ceric Ion Oxidation in Organic Chemistry. Synthesis 1973, 347–354
    • Synthesis , vol.1973 , pp. 347-354
    • Ho, T.-K.1
  • 52
    • 0011914936 scopus 로고
    • Removal of Thioacetal Protecting Groups by Cerium (IV) Ammonium Nitrate - Hydrolysis of 1,3-Dithiannes
    • Cristau, H.-J.; Chabaud, B.; Labaudiniere, R.; Christol, H. Removal of Thioacetal Protecting Groups by Cerium (IV) Ammonium Nitrate - Hydrolysis of 1,3-Dithiannes. Synth. Commun. 1981, 11, 423–428.
    • (1981) Synth. Commun. , vol.11 , pp. 423-428
    • Cristau, H.-J.1    Chabaud, B.2    Labaudiniere, R.3    Christol, H.4
  • 53
    • 26444589065 scopus 로고
    • Useful Dethioacetalization with Soft Acid Metal Salts: Thallium Trinitrate and Mercuric Perchlorate
    • Fujita, E.; Nagao, Y.; Kaneko, K. Useful Dethioacetalization with Soft Acid Metal Salts: Thallium Trinitrate and Mercuric Perchlorate. Chem. Pharm. Bull. 1978, 26, 3743–3751.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 3743-3751
    • Fujita, E.1    Nagao, Y.2    Kaneko, K.3
  • 55
    • 0000191346 scopus 로고
    • im-Tosylhistidine Derivatives as Starting Materials
    • im-Tosylhistidine Derivatives as Starting Materials. Bull. Chem. Soc. 1974, 47, 3146–3151.
    • (1974) Bull. Chem. Soc. , vol.47 , pp. 3146-3151
    • Fujii, T.1    Sakakibara, S.2
  • 56
    • 49549162927 scopus 로고
    • Diethylphosphoryl Cyanide. A New Reagent for the Synthesis of Amides
    • Yamada, S.; Kasai, Y.; Shioiri, T. Diethylphosphoryl Cyanide. A New Reagent for the Synthesis of Amides. Tetrahedron Lett. 1973, 14, 1595–1598.
    • (1973) Tetrahedron Lett. , vol.14 , pp. 1595-1598
    • Yamada, S.1    Kasai, Y.2    Shioiri, T.3
  • 58
    • 0022383821 scopus 로고
    • Difluorostatine- and Difluorostatone-Containing Peptides as Potent and Specific Renin Inhibitors
    • Thaisrivong, S.; Pals, D. T.; Kati, W. M.; Temer, S. R.; Thomasco, L. M. Difluorostatine- and Difluorostatone-Containing Peptides as Potent and Specific Renin Inhibitors. J. Med. Chem. 1985, 28, 1553–1555.
    • (1985) J. Med. Chem. , vol.28 , pp. 1553-1555
    • Thaisrivong, S.1    Pals, D.T.2    Kati, W.M.3    Temer, S.R.4    Thomasco, L.M.5
  • 59
    • 0022504190 scopus 로고
    • Design and Synthesis of Potent and Specific Renin Inhibitors Containing Difluorostatine, Difluorostatone, and Related Analogues
    • Thaisrivong, S.; Pals, D. T.; Kati, W. M.; Temer, S. R.; Thomasco, L. M.; Watt, W. Design and Synthesis of Potent and Specific Renin Inhibitors Containing Difluorostatine, Difluorostatone, and Related Analogues. J. Med. Chem. 1986, 29, 2080–2087.
    • (1986) J. Med. Chem. , vol.29 , pp. 2080-2087
    • Thaisrivong, S.1    Pals, D.T.2    Kati, W.M.3    Temer, S.R.4    Thomasco, L.M.5    Watt, W.6
  • 60
    • 0023405123 scopus 로고
    • Fluoro Ketone Containing Peptides as Inhibitors of Human Renin
    • Fearon, K.; Spaltenstein, A.; Hopkms, P. B.; Gelb, M. H. Fluoro Ketone Containing Peptides as Inhibitors of Human Renin. J. Med. Chem. 1987, 30, 1617–1622.
    • (1987) J. Med. Chem. , vol.30 , pp. 1617-1622
    • Fearon, K.1    Spaltenstein, A.2    Hopkms, P.B.3    Gelb, M.H.4
  • 63
    • 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


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