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Volumn 43, Issue 9, 2000, Pages 1705-1713

New proline mimetics: Synthesis of thrombin inhibitors incorporating cyclopentane- and cyclopentenedicarboxylic acid templates in the P2 position. Binding conformation investigated by X-ray crystallography

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; INOGATRAN; MELAGATRAN; N [4 [AMINO(IMINO)METHYL]BENZYL] 2 (1 PIPERIDINYLCARBONYL) 2 CYCLOPENTENE 1 CARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 (2' CARBOXYLBENZYL) 1,2 CYCLOPENTANEDICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 BENZYL 1,2 CYCLOPENTANEDICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 BENZYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYL 1,2 CYCLOPENTANEDICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYL N2 ETHOXY 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYL N2 ETHYL 1,2 CYCLOPENTANEDICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYL N2 ETHYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 CYCLOHEXYLMETHYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 PHENYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 PHENYL N2 ETHYL 2 CYCLOPENTENE 1,2 DICARBOXAMIDE; N1 [4 [AMINO(IMINO)METHYL]BENZYL] N2 [2' (METHYL)CARBOXYLBENZYL] 1,2 CYCLOPENTANEDICARBOXAMIDE; PROLINE DERIVATIVE; THROMBIN; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

EID: 0041424038     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990557t     Document Type: Article
Times cited : (30)

References (44)
  • 1
    • 0001334658 scopus 로고    scopus 로고
    • Design principles for orally bioavailable drugs
    • (a) Navia, M. A.; Chaturvedi, P. R. Design Principles for Orally Bioavailable Drugs. Drug Discovery Today 1996, 1, 179.
    • (1996) Drug Discovery Today , vol.1 , pp. 179
    • Navia, M.A.1    Chaturvedi, P.R.2
  • 4
    • 0031978808 scopus 로고    scopus 로고
    • Antithrombotic agents
    • Uzan, A. Antithrombotic Agents. Emerging Drugs 1998, 3, 189.
    • (1998) Emerging Drugs , vol.3 , pp. 189
    • Uzan, A.1
  • 5
    • 0026337077 scopus 로고
    • The coagulation cascade: Initiation, maintanance, and regulation
    • (a) Davie, E. W.; Fujikawa, K.; Kisiel, W. The Coagulation Cascade: Initiation, Maintanance, and Regulation. Biochemistry 1991, 30, 10363.
    • (1991) Biochemistry , vol.30 , pp. 10363
    • Davie, E.W.1    Fujikawa, K.2    Kisiel, W.3
  • 6
    • 0029099769 scopus 로고
    • Thrombin active site inhibitors
    • (b) Das, J.; Kimball, S. D. Thrombin Active Site Inhibitors. Bioorg. Med. Chem. 1995, 3, 999.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 999
    • Das, J.1    Kimball, S.D.2
  • 7
    • 0008760857 scopus 로고    scopus 로고
    • Energetic dissection of specificity in serine proteases
    • Springer-Verlag: ISBN 3-540-63250-6
    • (c) Di Cera, E.; Vindigni, A.; Banerjee, D. Energetic Dissection of Specificity in Serine Proteases. Structure-Based Drug Design; Springer-Verlag: ISBN 3-540-63250-6, 1997; pp 19-84.
    • (1997) Structure-Based Drug Design , pp. 19-84
    • Di Cera, E.1    Vindigni, A.2    Banerjee, D.3
  • 11
    • 0029122633 scopus 로고
    • Thrombin inhibitors. A new generation of antithrombotics
    • (d) Stone, S. R. Thrombin inhibitors. A New Generation of Antithrombotics. Trends Cardiovasc. Med. 1995, 5, 134.
    • (1995) Trends Cardiovasc. Med. , vol.5 , pp. 134
    • Stone, S.R.1
  • 12
    • 0013481920 scopus 로고    scopus 로고
    • Antithrombotics/Serine proteases
    • Bristol, J. A., Ed.; Academic: San Diego
    • (e) Ripka, W. C.; Vlasuk, G. P. Antithrombotics/Serine Proteases. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic: San Diego, 1997; Vol. 32, pp 71-89.
    • (1997) Annual Reports in Medicinal Chemistry , vol.32 , pp. 71-89
    • Ripka, W.C.1    Vlasuk, G.P.2
  • 13
    • 0030693694 scopus 로고    scopus 로고
    • Small-molecule direct thrombin inhibitors
    • (f) Wiley, M. R.; Fisher, M. J. Small-molecule Direct Thrombin Inhibitors. Exp. Opin. Ther. Patents 1997, 7, 1265.
    • (1997) Exp. Opin. Ther. Patents , vol.7 , pp. 1265
    • Wiley, M.R.1    Fisher, M.J.2
  • 14
    • 0008782050 scopus 로고
    • The story of D-Phe-Pro-Arg-H, the likely anticoagulant of the future
    • Bajusz, S. The Story of D-Phe-Pro-Arg-H, the Likely Anticoagulant of the Future. Biokémia 1990, 14, 127.
    • (1990) Biokémia , vol.14 , pp. 127
    • Bajusz, S.1
  • 15
    • 0029866371 scopus 로고    scopus 로고
    • Effects of inogatran, a new low-molecular weight thombin inhibitor, in rat models of venous and arterial thrombosis, thrombolysis and bleeding time
    • (a) Gustafsson, D.; Elg, M.; Lenfors, S.; Borjesson, I.; TegerNilsson, A. C. Effects of Inogatran, a new Low-Molecular Weight Thombin Inhibitor, in Rat Models of Venous and Arterial Thrombosis, Thrombolysis and Bleeding Time. Blood Coag. Fibrinolysis 1996, 7, 69.
    • (1996) Blood Coag. Fibrinolysis , vol.7 , pp. 69
    • Gustafsson, D.1    Elg, M.2    Lenfors, S.3    Borjesson, I.4    TegerNilsson, A.C.5
  • 16
    • 0030932442 scopus 로고    scopus 로고
    • In vitro effects of inogatran, a selective low molecular weight thrombin inhibitor
    • (b) TegerNilsson, A. C.; Bylund, R.; Gustafsson, D.; Gyzander, E.; Eriksson, U. In vitro Effects of Inogatran, a Selective Low Molecular Weight Thrombin Inhibitor. Thromb. Res. 1997, 85, 133.
    • (1997) Thromb. Res. , vol.85 , pp. 133
    • TegerNilsson, A.C.1    Bylund, R.2    Gustafsson, D.3    Gyzander, E.4    Eriksson, U.5
  • 17
    • 0000697152 scopus 로고    scopus 로고
    • Intravenous treatment of acute Deep Venous Thrombosis (DVT) with melagatran, a synthetic low molecular weight thrombin inhibitor
    • (a) Eriksson, H.; Eriksson, U.; Frison, L.; Thorsen, M. Intravenous treatment of Acute Deep Venous Thrombosis (DVT) with Melagatran, a Synthetic Low Molecular Weight Thrombin Inhibitor. Thromb. Haemostasis 1997, (Suppl.) OC-2411.
    • (1997) Thromb. Haemostasis , Issue.SUPPL.
    • Eriksson, H.1    Eriksson, U.2    Frison, L.3    Thorsen, M.4
  • 18
    • 0030771611 scopus 로고    scopus 로고
    • Antithrombotic effect of two low molecular weight thrombin inhibitors and a low-molecular weight heparin in a caval vein thrombosis model in the rat
    • (b) Eriksson, B. I.; Carlsson, S.; Halvarsson, M.; Risberg, B.; Mattsson, C. Antithrombotic Effect of Two Low Molecular Weight Thrombin Inhibitors and a Low-Molecular Weight Heparin in a Caval Vein Thrombosis Model in the Rat. Thromb. Haemostasis 1997, 78, 1404.
    • (1997) Thromb. Haemostasis , vol.78 , pp. 1404
    • Eriksson, B.I.1    Carlsson, S.2    Halvarsson, M.3    Risberg, B.4    Mattsson, C.5
  • 23
    • 0000983397 scopus 로고    scopus 로고
    • Enantio- and regioselective synthesis of a (Z)-Alkene cis-proline mimic
    • Hart, S. A.; Sabat, M.; Etzkorn, F. A. Enantio- and Regioselective Synthesis of a (Z)-Alkene cis-Proline Mimic. J. Org. Chem. 1998, 63, 7580-7581.
    • (1998) J. Org. Chem. , vol.63 , pp. 7580-7581
    • Hart, S.A.1    Sabat, M.2    Etzkorn, F.A.3
  • 24
    • 0343869748 scopus 로고
    • Resolution of trans-cydopentane-1:2-Dicarboxylic acid
    • Goldsworthy, L. J.; Perkin, W. H. Resolution of trans-Cydopentane-1:2-Dicarboxylic Acid. J. Chem. Soc. 1914, 2639.
    • (1914) J. Chem. Soc. , pp. 2639
    • Goldsworthy, L.J.1    Perkin, W.H.2
  • 25
    • 0023359751 scopus 로고
    • Enzymes and catalysts. I. Pig liver esterase-catalyzed hydrolysis of heterocyclic diesters
    • Morimoto, Y.; Terao, Y.; Achiwa, K. Enzymes and Catalysts. I. Pig Liver Esterase-Catalyzed Hydrolysis of Heterocyclic Diesters. Chem. Pharm. Bull. 1987, 35, 2266.
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 2266
    • Morimoto, Y.1    Terao, Y.2    Achiwa, K.3
  • 26
    • 84987368190 scopus 로고
    • Synthesis and first applications of a new chiral auxiliary (tert-Butyl 2-(tert-Butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate)
    • (a) Studer, A.; Hintermann, T.; Seebach, D. Synthesis and First Applications of a New Chiral Auxiliary (tert-Butyl 2-(tert-Butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate). Helv. Chim. Acta 1995, 78, 1185.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 1185
    • Studer, A.1    Hintermann, T.2    Seebach, D.3
  • 27
    • 0000706212 scopus 로고
    • Stereochemical aspects of the intramolecular diels-alder reactions of deca-2,7,9-trienoate esters. 3. Thermal lewis acid catalyzed, and asymmetric cyclizations
    • (b) Roush, W. R.; Gillis, H. R.; Ko, A. I. Stereochemical Aspects of the Intramolecular Diels-Alder Reactions of Deca-2,7,9-trienoate Esters. 3. Thermal Lewis Acid Catalyzed, and Asymmetric Cyclizations. J. Am. Chem. Soc. 1982, 104, 2269.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2269
    • Roush, W.R.1    Gillis, H.R.2    Ko, A.I.3
  • 28
    • 0026414035 scopus 로고
    • Synthesis of optically pure di-to tetra-substituted cyclopentanes from sugar-derived norbornene derivatives
    • (c) Horton, D.; Usui, T. Synthesis of Optically Pure di-to tetra-Substituted Cyclopentanes from Sugar-Derived Norbornene Derivatives. Carbohydr. Res. 1991, 51.
    • (1991) Carbohydr. Res. , pp. 51
    • Horton, D.1    Usui, T.2
  • 29
    • 0029041562 scopus 로고
    • Diastereoselective oxidative coupling of chiral carboxylic acid derivatives
    • (d) Langer, T.; Illich, M.; Helmchen, G. Diastereoselective Oxidative Coupling of Chiral Carboxylic Acid Derivatives. Tetrahedron Lett. 1995, 36, 4409.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4409
    • Langer, T.1    Illich, M.2    Helmchen, G.3
  • 30
    • 0001690896 scopus 로고
    • Simple asymmetric construction of carbocyclic framework. Direct coupling of dimenthyl succinate with 1,ω-dihalides
    • (d) Misumi, A.; Iwanaga, K.; Furuta, K. Yamamoto, H. Simple Asymmetric Construction of Carbocyclic Framework. Direct Coupling of Dimenthyl Succinate with 1,ω-Dihalides. J. Am. Chem. Soc. 1985, 107, 3343.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3343
    • Misumi, A.1    Iwanaga, K.2    Furuta, K.3    Yamamoto, H.4
  • 31
    • 0002299370 scopus 로고
    • Condensation of (-)-Dimenthyl succinate dianion with 1,ω-Dihalides: (-)-(1S,2S)-Cyclopropane-1,2-Dicarboxylic acid
    • (e) Furuta, K.; Iwanaga, K.; Yamamoto, H. Condensation of (-)-Dimenthyl Succinate Dianion with 1,ω-Dihalides: (-)-(1S,2S)-Cyclopropane-1,2-Dicarboxylic Acid. Org. Synth. 1988, 67, 76.
    • (1988) Org. Synth. , vol.67 , pp. 76
    • Furuta, K.1    Iwanaga, K.2    Yamamoto, H.3
  • 32
    • 0039077193 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors
    • (a) Nöteberg, D.; Brånalt, J.; Kvarnström, I.; Classon, B.; Samuelsson, B.; Nillroth, U.; Danielson, U. H.; Karlén, A.; Hallberg, A. Synthesis of Enantiomerically Pure cis and trans 2-Aminocyclopentanecarboxylic Acids. Use of Proline Replacements in Potential HIV-Protease Inhibitors. Tetrahedron 1997, 53, 7975.
    • (1997) Tetrahedron , vol.53 , pp. 7975
    • Nöteberg, D.1    Brånalt, J.2    Kvarnström, I.3    Classon, B.4    Samuelsson, B.5    Nillroth, U.6    Danielson, U.H.7    Karlén, A.8    Hallberg, A.9
  • 33
    • 0001037193 scopus 로고
    • Synthesis of enantiomerically pure trans-3,4-substituted cyclopentanols by enzymatic resolution
    • (b) Rosenquist, Å.; Kvarnström, I.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. Synthesis of Enantiomerically Pure trans-3,4-Substituted Cyclopentanols by enzymatic resolution. Acta Chem. Scand. 1992, 46, 1127.
    • (1992) Acta Chem. Scand. , vol.46 , pp. 1127
    • Rosenquist, A.1    Kvarnström, I.2    Svensson, S.C.T.3    Classon, B.4    Samuelsson, B.5
  • 34
    • 85099487902 scopus 로고    scopus 로고
    • note
    • 13b
  • 35
    • 85099489062 scopus 로고    scopus 로고
    • note
    • 13c
  • 36
    • 0031794772 scopus 로고    scopus 로고
    • Large scale preparation of protected 4-Aminomethylbenzamidine. Application to the synthesis of the thrombin inhibitor, melagatran
    • Lila, C.; Gloanc, P.; Cadet, L.; Hervé, Y.; Fournier. J.; Leborgne, F.; Verbeuren, T. J.; De Nanteuil, G. Large Scale Preparation of Protected 4-Aminomethylbenzamidine. Application to the Synthesis of the Thrombin Inhibitor, Melagatran. Synth. Commun. 1998, 28, 4419.
    • (1998) Synth. Commun. , vol.28 , pp. 4419
    • Lila, C.1    Gloanc, P.2    Cadet, L.3    Hervé, Y.4    Fournier, J.5    Leborgne, F.6    Verbeuren, T.J.7    De Nanteuil, G.8
  • 37
    • 0343433985 scopus 로고    scopus 로고
    • note
    • For compound 6 the reaction sequence was altered: the coupling product was treated with NaOH in aqueous dioxane to hydrolyze the ester prior to the hydrogenation step.
  • 40
    • 85099487919 scopus 로고    scopus 로고
    • note
    • 19 shows that the absolute configuration of this bisester is S. Chiral HPLC showed that (-)-11 and (+)-11 had an ee > 90%.
  • 42
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray diffraction data collected in oscillation mode
    • Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 1997, 276, 307.
    • (1997) Methods Enzymol. , vol.276 , pp. 307
    • Otwinowski, Z.1    Minor, W.2
  • 43
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project, Number 4. The CCP4 Suite: Programs for Protein Crystallography. Acta Crystallogr. 1994, D50, 760.
    • (1994) Acta Crystallogr. , vol.D50 , pp. 760


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