메뉴 건너뛰기




Volumn 48, Issue 9, 2005, Pages 3110-3113

Toward a novel class of antithrombotic compounds with dual function. Discovery of 1,4-benzoxazin-3(4H)-one derivatives possessing thrombin inhibitory and fibrinogen receptor antagonistic activities

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOXAZIN 3(4H) ONE DERIVATIVE; ACETYLSALICYLIC ACID; ADENOSINE DIPHOSPHATE; ANTITHROMBOCYTIC AGENT; ARGATROBAN; ARGINYLGLYCYLASPARTIC ACID; BENZOXAZINE DERIVATIVE; BLOOD CLOTTING FACTOR 10A INHIBITOR; COLLAGEN; FIBRINOGEN; FIBRINOGEN RECEPTOR; FIBRINOGEN RECEPTOR ANTAGONIST; HEPARIN; THROMBIN INHIBITOR; TICLOPIDINE; UNCLASSIFIED DRUG; WARFARIN; XIMELAGATRAN;

EID: 18244394034     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm048984g     Document Type: Article
Times cited : (62)

References (33)
  • 1
    • 0030983708 scopus 로고    scopus 로고
    • Mortality by cause for eight regions of the world: Global burden of disease study
    • Murray, C. J. L.; Lopez, A. D. Mortality by cause for eight regions of the world: global burden of disease study. Lancet 1997, 349, 1269-1276.
    • (1997) Lancet , vol.349 , pp. 1269-1276
    • Murray, C.J.L.1    Lopez, A.D.2
  • 2
    • 0037797327 scopus 로고    scopus 로고
    • New antithrombotic drugs on the horizon
    • Ruef, J.; Katus, H. A. New antithrombotic drugs on the horizon. Expert Opin. Invest. Drugs 2003, 12, 781-797.
    • (2003) Expert Opin. Invest. Drugs , vol.12 , pp. 781-797
    • Ruef, J.1    Katus, H.A.2
  • 3
    • 4444257019 scopus 로고    scopus 로고
    • Progress in the development of synthetic thrombin inhibitors as new orally active anticoagulants
    • Steinmetzer, T.; Stürzebecher, J. Progress in the development of synthetic thrombin inhibitors as new orally active anticoagulants. Curr. Med. Chem. 2004, 11, 2297-2321.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 2297-2321
    • Steinmetzer, T.1    Stürzebecher, J.2
  • 4
    • 0141954082 scopus 로고    scopus 로고
    • Recent advances in the discovery and development of direct coagulation factor Xa inhibitors
    • Gould, W. R. Recent advances in the discovery and development of direct coagulation Factor Xa inhibitors. Curr. Pharm. Des. 2003, 9, 2337-2347.
    • (2003) Curr. Pharm. Des. , vol.9 , pp. 2337-2347
    • Gould, W.R.1
  • 5
    • 2342559976 scopus 로고    scopus 로고
    • Peptidomimetics-antagonists of the fibrinogen receptor: Molecular design, structures, properties and therapeutic applications
    • Andronati, S. A.; Karaseva, T. L.; Krysko, A. A. Peptidomimetics- Antagonists of the fibrinogen receptor: Molecular design, structures, properties and therapeutic applications. Curr. Med. Chem. 2004, 11, 1183-1211.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 1183-1211
    • Andronati, S.A.1    Karaseva, T.L.2    Krysko, A.A.3
  • 6
    • 0024431034 scopus 로고
    • The refined 1.9 Å crystal structure of human α-thrombin: Interaction with D-Phe-Pro-Arg chloromethyl ketone and significance of the Tyr-Pro-Pro-Trp insertion segment
    • Bode, W.; Mayr, I.; Baumann, U.; Huber, R.; Stone, S. R.; Hofsteenge, J. The refined 1.9 Å crystal structure of human α-thrombin: interaction with D-Phe-Pro-Arg chloromethyl ketone and significance of the Tyr-Pro-Pro-Trp insertion segment. EMBO J. 1989, 8, 3467-3475.
    • (1989) EMBO J. , vol.8 , pp. 3467-3475
    • Bode, W.1    Mayr, I.2    Baumann, U.3    Huber, R.4    Stone, S.R.5    Hofsteenge, J.6
  • 7
    • 1842854553 scopus 로고    scopus 로고
    • Ximelagatran: The first oral direct thrombin inhibitor
    • Crowther M. A.; Weitz, J. I. Ximelagatran: the first oral direct thrombin inhibitor. Expert Opin. Invest. Drugs 2004, 13, 403-413.
    • (2004) Expert Opin. Invest. Drugs , vol.13 , pp. 403-413
    • Crowther, M.A.1    Weitz, J.I.2
  • 8
    • 0029067684 scopus 로고
    • Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp sequence of fibrinogen. (Aminobenzamidmo)succinyl (ABAS) series of orally active fibrinogen receptor antagonists
    • Zablocki, A. J.; Rico, J. G.; Garland, R. B. et al. Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp sequence of fibrinogen. (Aminobenzamidmo)succinyl (ABAS) series of orally active fibrinogen receptor antagonists. J. Med. Chem. 1995, 38, 2378-2394.
    • (1995) J. Med. Chem. , vol.38 , pp. 2378-2394
    • Zablocki, A.J.1    Rico, J.G.2    Garland, R.B.3
  • 9
    • 0032198438 scopus 로고    scopus 로고
    • ACC/AHA guidelines for the management of patients with valvular heart disease
    • Bonow, R. O.; Carabello, B.; de Leon, A. C. et al. ACC/AHA Guidelines for the management of patients with valvular heart disease. J. Heart Valve Dis. 1998, 7, 672-707.
    • (1998) J. Heart Valve Dis. , vol.7 , pp. 672-707
    • Bonow, R.O.1    Carabello, B.2    De Leon, A.C.3
  • 10
    • 0028346254 scopus 로고
    • Combination of platelet fibrinogen receptor antagonist and direct thrombin inhibitor at low dosis markedly improves thrombolysis
    • Nicolini, F. A.; Lee, P.; Rios, G.; Kottke-Marchant, K.; Topol, E. J. Combination of platelet fibrinogen receptor antagonist and direct thrombin inhibitor at low dosis markedly improves thrombolysis. Circulation 1994, 89, 1802-1809.
    • (1994) Circulation , vol.89 , pp. 1802-1809
    • Nicolini, F.A.1    Lee, P.2    Rios, G.3    Kottke-Marchant, K.4    Topol, E.J.5
  • 11
    • 0033760658 scopus 로고    scopus 로고
    • Combination of a direct thrombin inhibitor and a platelet glycoprotein IIb/IIIa blocking peptide facilitates and maintaines reperfusion of platelet-rich thrombus with alteplase
    • Sabatine, M. S.; Tu, T. M.; Jang, I.-K. Combination of a direct thrombin inhibitor and a platelet glycoprotein IIb/IIIa blocking peptide facilitates and maintaines reperfusion of platelet-rich thrombus with alteplase. J. Thromb. Thrombolysis 2000, 10, 189-196.
    • (2000) J. Thromb. Thrombolysis , vol.10 , pp. 189-196
    • Sabatine, M.S.1    Tu, T.M.2    Jang, I.-K.3
  • 12
    • 0032895104 scopus 로고    scopus 로고
    • Clinical experience with combined treatment of thrombin inhibitors and GP IIb/IIIa inhibitors in patients with HIT
    • Wallenga, J. M.; Jeske, W. P.; Wallis, D. E.; Bakhos, M.; Lewis, B. E.; Leya, F.; Fareed, J. Clinical experience with combined treatment of thrombin inhibitors and GP IIb/IIIa inhibitors in patients with HIT. Semin. Thromb. Hemostasis 1999, 25, Suppl. 1, 77-81.
    • (1999) Semin. Thromb. Hemostasis , vol.25 , Issue.SUPPL. 1 , pp. 77-81
    • Wallenga, J.M.1    Jeske, W.P.2    Wallis, D.E.3    Bakhos, M.4    Lewis, B.E.5    Leya, F.6    Fareed, J.7
  • 13
    • 0037453968 scopus 로고    scopus 로고
    • Bivalirudin and provisional glycoprotein IIb/IIIa blockade compared with heparin and planned glycoprotein IIb/IIIa blockade during percutaneous coronary intervention-REPLACE-2 randomized trial
    • Lincoff, A. M.; Bittl, J. A.; Harrington, R. A. et al. Bivalirudin and provisional glycoprotein IIb/IIIa blockade compared with heparin and planned glycoprotein IIb/IIIa blockade during percutaneous coronary intervention- REPLACE-2 randomized trial. JAMA 2003, 289, 853-863.
    • (2003) JAMA , vol.289 , pp. 853-863
    • Lincoff, A.M.1    Bittl, J.A.2    Harrington, R.A.3
  • 14
    • 3242794178 scopus 로고    scopus 로고
    • From magic bullets to designed multiple ligands
    • Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands. Drug Discovery Today 2004, 9, 641-651.
    • (2004) Drug Discovery Today , vol.9 , pp. 641-651
    • Morphy, R.1    Kay, C.2    Rankovic, Z.3
  • 15
    • 0025951849 scopus 로고
    • Chimeric antithrombin peptide-characterization of an Arg-Gly-Asp (RGD)-containing and hirudin carboxyl terminus-containing synthetic peptide
    • Church, F. C.; Phillips, J. E.; Woods, J. L. Chimeric antithrombin peptide-Characterization of an Arg-Gly-Asp (RGD)-containing and hirudin carboxyl terminus-containing synthetic peptide. J. Biol. Chem. 1991, 266, 11975-11979.
    • (1991) J. Biol. Chem. , vol.266 , pp. 11975-11979
    • Church, F.C.1    Phillips, J.E.2    Woods, J.L.3
  • 16
    • 18244384433 scopus 로고    scopus 로고
    • Trifunctional antithrombin and antiplatelet peptides. WO9429349, 1994
    • Owen, T. J.; Broersma, R. J., Jr; Krstenansky, J. L. Trifunctional antithrombin and antiplatelet peptides. WO9429349, 1994.
    • Owen, T.J.1    Broersma Jr., R.J.2    Krstenansky, J.L.3
  • 17
    • 18244399316 scopus 로고    scopus 로고
    • Pharmacological characterization of BIBR 830ZW: A novel, low molecular weight, synthetic combined inhibitor of thrombin, factor Xa and platelet aggregation
    • Presented at the 18th Congress of the International Society of Thrombosis and Haemostasis, July 6-12, 2001, Paris: Abstr. P756
    • Wienen, W.; Nar, H.; Ries, U. J.; Priepke, H. W. M.; Hauel, N. H.; Stassen, J. M. Pharmacological characterization of BIBR 830ZW: A novel, low molecular weight, synthetic combined inhibitor of thrombin, Factor Xa and platelet aggregation. Presented at the 18th Congress of the International Society of Thrombosis and Haemostasis, July 6-12, 2001, Paris. Thromb. Haemostasis 2001, Suppl.: Abstr. P756.
    • (2001) Thromb. Haemostasis , Issue.SUPPL.
    • Wienen, W.1    Nar, H.2    Ries, U.J.3    Priepke, H.W.M.4    Hauel, N.H.5    Stassen, J.M.6
  • 18
    • 18244393735 scopus 로고    scopus 로고
    • note
    • (a) Docking was performed with AutoDock Tools version 3.0.5.
  • 19
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • (b) Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Har, T. W. E.; Belew; R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Har, T.W.E.5    Belew, R.K.6    Olson, A.J.7
  • 20
    • 18244375791 scopus 로고    scopus 로고
    • note
    • 1 benzamidine moiety.
  • 21
    • 1842785009 scopus 로고    scopus 로고
    • Ximelagatran/melagatran - A review of its use in the prevention of venous thromboembolism in orthopaedic surgery
    • (b) Evans, H. C.; Perry, C. M.; Faulds; D. Ximelagatran/melagatran - A review of its use in the prevention of venous thromboembolism in orthopaedic surgery. Drugs 2004, 64, 649-678.
    • (2004) Drugs , vol.64 , pp. 649-678
    • Evans, H.C.1    Perry, C.M.2    Faulds, D.3
  • 22
    • 1842633720 scopus 로고    scopus 로고
    • Prevention of venous thromboembolism following orthopaedic surgery. Clinical potential of direct thrombin inhibitors
    • (c) Eriksson; B. I., Dahl, O. E. Prevention of venous thromboembolism following orthopaedic surgery. Clinical potential of direct thrombin inhibitors. Drugs 2004, 64, 577-595.
    • (2004) Drugs , vol.64 , pp. 577-595
    • Eriksson, B.I.1    Dahl, O.E.2
  • 23
    • 0004068080 scopus 로고    scopus 로고
    • Release 5.01 for Windows, Hypercube, Inc.
    • HyperChem (Release 5.01 for Windows, Hypercube, Inc. 1996).
    • (1996) HyperChem
  • 24
    • 0025837452 scopus 로고
    • Crystallographic analysis at 3.0-A resolution of the binding to human thrombin of four active site-directed inhibitors
    • Banner, D. W.; Hadvary, P. Crystallographic analysis at 3.0-A resolution of the binding to human thrombin of four active site-directed inhibitors. J. Biol. Chem. 1991, 266, 20085-20093.
    • (1991) J. Biol. Chem. , vol.266 , pp. 20085-20093
    • Banner, D.W.1    Hadvary, P.2
  • 25
    • 0020356946 scopus 로고
    • A facile synthesis of 2-alkyl(aryl)-6- and -7-nitro-3-oxo-3,4-dihydro-2H- 1,4-benzoxazines
    • Shridhar, D. R.; Gandhi, S. S.; Rao, S. K. A Facile synthesis of 2-alkyl(aryl)-6- and -7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazines Synthesis 1982, 986-987.
    • (1982) Synthesis , pp. 986-987
    • Shridhar, D.R.1    Gandhi, S.S.2    Rao, S.K.3
  • 26
    • 0031825959 scopus 로고    scopus 로고
    • Selective alkylation of 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2- carboxylates
    • Rutar, A.; Kikelj, D. Selective alkylation of 3-oxo-3,4-dihydro-2H-1,4- benzoxazine-2-carboxylates. Synth. Commun. 1998, 28, 2737-2749.
    • (1998) Synth. Commun. , vol.28 , pp. 2737-2749
    • Rutar, A.1    Kikelj, D.2
  • 27
    • 84986432000 scopus 로고
    • A simplified procedure for preparing 3,5-di-substituted-1,2,4-oxadiazoles by reaction of amidoximes with acyl chlorides in pyridine solution
    • Chiou, S.; Shine, H. J. A simplified procedure for preparing 3,5-di-substituted-1,2,4-oxadiazoles by reaction of amidoximes with acyl chlorides in pyridine solution. J. Heterocycl. Chem. 1989, 26, 125-128.
    • (1989) J. Heterocycl. Chem. , vol.26 , pp. 125-128
    • Chiou, S.1    Shine, H.J.2
  • 30
    • 0020655601 scopus 로고
    • The action of thrombin on peptide para-nitroanilide substrates - Substrate selectivity and examination of hydrolysis under different reaction conditions
    • (b) Lottenberg R.; Hall J. A.; Blinder M.; Binder E. P.; Jackson C. R. The action of thrombin on peptide para-nitroanilide substrates - substrate selectivity and examination of hydrolysis under different reaction conditions. Biochim. Biophys. Acta 1983, 742, 539-557.
    • (1983) Biochim. Biophys. Acta , vol.742 , pp. 539-557
    • Lottenberg, R.1    Hall, J.A.2    Blinder, M.3    Binder, E.P.4    Jackson, C.R.5
  • 31
    • 0037021332 scopus 로고    scopus 로고
    • Synthesis and biological investigation of novel tricyclic benzodiazepinedione-based RGD analogues
    • Addicks, E.; Mazitchek, R.; Giannis, A. Synthesis and biological investigation of novel tricyclic benzodiazepinedione-based RGD analogues. ChemBioChem 2002, 3, 1078-1088.
    • (2002) ChemBioChem , vol.3 , pp. 1078-1088
    • Addicks, E.1    Mazitchek, R.2    Giannis, A.3
  • 32
    • 0025369267 scopus 로고
    • Attempts to standardize platelet aggregation measurements: Simplified screening tests
    • (a) Kirchhof B.; Kirchhoff U.; Etsheid G. Attempts to standardize platelet aggregation measurements: Simplified screening tests. Haemostasis 1990, 20, 169-180.
    • (1990) Haemostasis , vol.20 , pp. 169-180
    • Kirchhof, B.1    Kirchhoff, U.2    Etsheid, G.3
  • 33
    • 0021797820 scopus 로고
    • Methods in dose response platelet aggregometry
    • (b) Thompson S. G., Vickers M. V. Methods in dose response platelet aggregometry. Thromb. Haemostasis 1985, 53, 216-218.
    • (1985) Thromb. Haemostasis , vol.53 , pp. 216-218
    • Thompson, S.G.1    Vickers, M.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.