메뉴 건너뛰기




Volumn 46, Issue 19, 2003, Pages 4050-4062

Design, parallel synthesis, and crystal structures of pyrazinone antithrombotics as selective inhibitors of the tissue factor VIIa complex

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 5 [1 [2 [[4 [AMINO(IMINO)METHYL]BENZYL]AMINO] 2 OXOETHYL] 3 CHLORO 5 (ISOPROPYLAMINO) 6 OXO 1,6 DIHYDROPYRAZIN 2 YL]BENZOIC ACID; ANTICOAGULANT AGENT; BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 7A; PYRAZINONE DERIVATIVE; THROMBIN; THROMBOPLASTIN; UNCLASSIFIED DRUG;

EID: 0043211876     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030131l     Document Type: Article
Times cited : (95)

References (68)
  • 1
    • 0036243671 scopus 로고    scopus 로고
    • Tissue Factor - A therapeutic target for thrombotic disorders
    • Houston, D. S. Tissue Factor - a therapeutic target for thrombotic disorders. Expert Opin. Ther. Targets 2002, 6, 159-174.
    • (2002) Expert Opin. Ther. Targets , vol.6 , pp. 159-174
    • Houston, D.S.1
  • 2
    • 0036588702 scopus 로고    scopus 로고
    • The inhibitors of the tissue Factor: Factor VII pathway
    • Golino, P. The inhibitors of the tissue Factor: Factor VII pathway. Thromb. Res. 2002, 106, V257-V265.
    • (2002) Thromb. Res. , vol.106
    • Golino, P.1
  • 3
  • 4
    • 0035169891 scopus 로고    scopus 로고
    • Tissue factor pathway inhibitor: An update of potential implications in the treatment of cardiovascular disorders
    • Kaiser, B.; Hoppensteadt, D. A.; Fareed, J. Tissue factor pathway inhibitor: an update of potential implications in the treatment of cardiovascular disorders. Expert Opin. Invest. Drugs 2001, 10, 1925-1935.
    • (2001) Expert Opin. Invest. Drugs , vol.10 , pp. 1925-1935
    • Kaiser, B.1    Hoppensteadt, D.A.2    Fareed, J.3
  • 5
    • 0035321911 scopus 로고    scopus 로고
    • The role of tissue Factor/Factor VIIa in the pathophysiology of acute thrombotic formation
    • Girard, T. J.; Nicholson, N. S. The role of tissue Factor/Factor VIIa in the pathophysiology of acute thrombotic formation. Curr. Opin. Pharmacol. 2001, 1, 159-163.
    • (2001) Curr. Opin. Pharmacol. , vol.1 , pp. 159-163
    • Girard, T.J.1    Nicholson, N.S.2
  • 6
    • 0034648757 scopus 로고    scopus 로고
    • Thrombin signaling and protease-activated receptors
    • Coughlin, S. R. Thrombin signaling and protease-activated receptors. Nature 2000, 407, 258-264.
    • (2000) Nature , vol.407 , pp. 258-264
    • Coughlin, S.R.1
  • 7
    • 0042571135 scopus 로고    scopus 로고
    • Tissue factor pathway inhibitor
    • Sasahara, A. A., and Loscalzo, J., Eds.; Marcel Dekker: New York
    • Girard, T. J. Tissue Factor Pathway Inhibitor. In New Therapeutic Agents in Thrombosis and Thrombolysis; Sasahara, A. A., and Loscalzo, J., Eds.; Marcel Dekker: New York, 1998.
    • (1998) New Therapeutic Agents in Thrombosis and Thrombolysis
    • Girard, T.J.1
  • 8
    • 0030805621 scopus 로고    scopus 로고
    • The Factor VIIa/tissue Factor complex
    • Banner, D. W. The Factor VIIa/tissue Factor complex. Thromb. Haemost. 1997, 78, 512-515.
    • (1997) Thromb. Haemost. , vol.78 , pp. 512-515
    • Banner, D.W.1
  • 9
    • 0030221068 scopus 로고    scopus 로고
    • Initiation of blood coagulation: The tissue Factor/Factor VIIa complex
    • Kirchhofer, D.; Nemerson, Y. Initiation of blood coagulation: the tissue Factor/Factor VIIa complex. Curr. Opin. Chem. Biotech. 1996, 7, 386-391.
    • (1996) Curr. Opin. Chem. Biotech. , vol.7 , pp. 386-391
    • Kirchhofer, D.1    Nemerson, Y.2
  • 10
    • 0029063995 scopus 로고
    • Regulation of the extrinsic pathway system in health and disease: The role of Factor VIIa and tissue factor pathway inhibitor
    • Petersen, L. C.; Valentin, S.; Hedner, U. Regulation of the extrinsic pathway system in health and disease: the role of Factor VIIa and tissue factor pathway inhibitor. Thromb. Res. 1995, 79, 1-47.
    • (1995) Thromb. Res. , vol.79 , pp. 1-47
    • Petersen, L.C.1    Valentin, S.2    Hedner, U.3
  • 12
    • 0025875990 scopus 로고
    • The structural biology of expression and function of tissue factor
    • Edgington, T. S.; Mackman, N.; Brand, K.; Ruf, W. The structural biology of expression and function of tissue factor. Thromb. Haemost. 1991, 66, 67-79.
    • (1991) Thromb. Haemost. , vol.66 , pp. 67-79
    • Edgington, T.S.1    Mackman, N.2    Brand, K.3    Ruf, W.4
  • 13
    • 0002362826 scopus 로고    scopus 로고
    • Anticoagulants: Inhibitors of thrombin and Factor Xa
    • Sanderson, P. E. J. Anticoagulants: Inhibitors of thrombin and Factor Xa. Annu. Rep. Med. Chem. 2001, 36, 79-88.
    • (2001) Annu. Rep. Med. Chem. , vol.36 , pp. 79-88
    • Sanderson, P.E.J.1
  • 14
    • 0034976145 scopus 로고    scopus 로고
    • Recent advances in Factor Xa inhibitors
    • Betz, A. Recent advances in Factor Xa inhibitors. Expert Opin. Ther. Pat. 2001, 11, 1007-1017.
    • (2001) Expert Opin. Ther. Pat. , vol.11 , pp. 1007-1017
    • Betz, A.1
  • 15
    • 3042749886 scopus 로고    scopus 로고
    • Factor Xa inhibitors: Recent advances in anticoagulant agents
    • Zhu, B. Y.; Scarborough, R. M. Factor Xa inhibitors: Recent advances in anticoagulant agents. Annu. Rep. Med. Chem. 2000, 35 83-102.
    • (2000) Annu. Rep. Med. Chem. , vol.35 , pp. 83-102
    • Zhu, B.Y.1    Scarborough, R.M.2
  • 16
    • 0033859659 scopus 로고    scopus 로고
    • New Advances in the discovery of Thrombin and Factor Xa inhibitors
    • Vacca, J. P. New Advances in the discovery of Thrombin and Factor Xa inhibitors. Curr. Opin. Chem. Biol. 2000, 4, 394-400.
    • (2000) Curr. Opin. Chem. Biol. , vol.4 , pp. 394-400
    • Vacca, J.P.1
  • 17
    • 0033017497 scopus 로고    scopus 로고
    • Small, noncovalent serine protease inhibitors
    • Sanderson, P. E. J. Small, noncovalent serine protease inhibitors. Med. Res. Rev. 1999, 19, 179-197.
    • (1999) Med. Res. Rev. , vol.19 , pp. 179-197
    • Sanderson, P.E.J.1
  • 18
    • 0032831727 scopus 로고    scopus 로고
    • Progress in the design of inhibitors of coagulation Factor Xa
    • Ewing, W. R.; Pauls, H. W.; Spada, A. P. Progress in the design of inhibitors of coagulation Factor Xa. Drugs Future 1999, 24, 771-787.
    • (1999) Drugs Future , vol.24 , pp. 771-787
    • Ewing, W.R.1    Pauls, H.W.2    Spada, A.P.3
  • 20
    • 0037073167 scopus 로고    scopus 로고
    • Total synthesis and structural confirmation of the marine natural product Dysinosin A: A novel inhibitor of thrombin and Factor VIIa
    • Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. Total synthesis and structural confirmation of the marine natural product Dysinosin A: A novel inhibitor of thrombin and Factor VIIa. J. Am. Chem. Soc. 2002, 124, 13342-13343.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13342-13343
    • Hanessian, S.1    Margarita, R.2    Hall, A.3    Johnstone, S.4    Tremblay, M.5    Parlanti, L.6
  • 21
    • 0037152493 scopus 로고    scopus 로고
    • Targeting thrombin and Factor VIIa: Design, synthesis, and inhibitory activity of functionally relevant indolizidinones
    • Hanessian, S.; Therrien, E.; Granberg, K.; Nilsson, I. Targeting thrombin and Factor VIIa: design, synthesis, and inhibitory activity of functionally relevant indolizidinones. Bioorg. Med. Chem. Lett. 2002, 12, 2907-2911.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2907-2911
    • Hanessian, S.1    Therrien, E.2    Granberg, K.3    Nilsson, I.4
  • 23
    • 0034609147 scopus 로고    scopus 로고
    • An efficient synthesis of 2-[3-(4-amidinophenylcarbamoyl)naphthalen-2-yl]-5-[(2,2-methylpropyl)carbamoyl] benzoic acid: A Factor VIIa inhibitor discovered by the Ono Pharmaceutical Company
    • Kohrt, J. T.; Filipski, K. J.; Rapundalo, S. T.; Cody, W. L.; Edmunds, J. J. An efficient synthesis of 2-[3-(4-amidinophenylcarbamoyl)naphthalen-2-yl]-5-[(2,2-methylpropyl)carbamoyl] benzoic acid: a Factor VIIa inhibitor discovered by the Ono Pharmaceutical Company. Tetrahedron Lett. 2000, 41, 6041-6044.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6041-6044
    • Kohrt, J.T.1    Filipski, K.J.2    Rapundalo, S.T.3    Cody, W.L.4    Edmunds, J.J.5
  • 24
    • 0033763192 scopus 로고    scopus 로고
    • Inhibitors of the tissue Factor/Factor VIIa-induced coagulation: Synthesis and in vitro evaluation of novel 2-aryl substituted pyrido[3,4-d][1,3]-, pyrido[2,3-d][1,3]-, pyrazino[2,3-d][1,3]-, pyrimido[4,5-d][1,3]-, pyrazolo[3,4-d][1,3]-, thieno[3,2-d][1,3]- and thieno[2,3-d][1,3]-oxazin-4-ones
    • Jakobsen, P.; Horneman, A. M.; Persson, E. Inhibitors of the tissue Factor/Factor VIIa-induced coagulation: synthesis and in vitro evaluation of novel 2-aryl substituted pyrido[3,4-d][1,3]-, pyrido[2,3-d][1,3]-, pyrazino[2,3-d][1,3]-, pyrimido[4,5-d][1,3]-, pyrazolo[3,4-d][1,3]-, thieno[3,2-d][1,3]- and thieno[2,3-d][1,3]-oxazin-4-ones. Bioorg. Med. Chem. 2000, 8, 2803-2812.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2803-2812
    • Jakobsen, P.1    Horneman, A.M.2    Persson, E.3
  • 25
    • 0033866734 scopus 로고    scopus 로고
    • Inhibitors of the tissue Factor/Factor VIIa-induced coagulation: Synthesis and in vitro evaluation of novel specific 2-aryl substituted 4H-3,1-benzoxazin-4-ones
    • Jakobsen, P.; Ritsmar Pedersen, B.; Persson, E. Inhibitors of the tissue Factor/Factor VIIa-induced coagulation: synthesis and in vitro evaluation of novel specific 2-aryl substituted 4H-3,1-benzoxazin-4-ones. Bioorg. Med. Chem. 2000, 8, 2095-2103.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2095-2103
    • Jakobsen, P.1    Ritsmar Pedersen, B.2    Persson, E.3
  • 26
    • 0033531977 scopus 로고    scopus 로고
    • Inhibition of the tissue Factor/Factor VIIa complex: Lead optimization using combinatorial chemistry
    • Roussel, P.; Bradley, M.; Kane, P.; Bailey, C.; Arnold, R.; Cross, A. Inhibition of the tissue Factor/Factor VIIa complex: lead optimization using combinatorial chemistry. Tetrahedron 1999, 55, 6219-6230.
    • (1999) Tetrahedron , vol.55 , pp. 6219-6230
    • Roussel, P.1    Bradley, M.2    Kane, P.3    Bailey, C.4    Arnold, R.5    Cross, A.6
  • 28
    • 0031730809 scopus 로고    scopus 로고
    • Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue Factor-Factor VIIa complex
    • Wang, D.; Girard, T. J.; Kasten, T. P.; LaChance, R. M.; Miller-Wideman, M. A.; Durley, R. C. Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue Factor-Factor VIIa complex. J. Nat. Prod. 1998, 61, 1352-1355.
    • (1998) J. Nat. Prod. , vol.61 , pp. 1352-1355
    • Wang, D.1    Girard, T.J.2    Kasten, T.P.3    LaChance, R.M.4    Miller-Wideman, M.A.5    Durley, R.C.6
  • 29
    • 0031552099 scopus 로고    scopus 로고
    • Synthesis and biological activity of P2-P4 azapeptidomimetic P1-argininal and P1-ketoargininamide derivatives: A novel class of serine protease inhibitors
    • Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Ripka, W. C. Synthesis and biological activity of P2-P4 azapeptidomimetic P1-argininal and P1-ketoargininamide derivatives: a novel class of serine protease inhibitors. Bioorg. Med. Chem. Lett. 1997, 7, 315-320.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 315-320
    • Semple, J.E.1    Rowley, D.C.2    Brunck, T.K.3    Ripka, W.C.4
  • 30
    • 0027989457 scopus 로고
    • Effect of nafamostat mesylate, a synthetic protease inhibitor, on tissue Factor-Factor VIIa complex activity
    • Uchiba, M.; Okajima, K.; Abe, H.; Okabe, H.; Takatsuki, K. Effect of nafamostat mesylate, a synthetic protease inhibitor, on tissue Factor-Factor VIIa complex activity. Thromb. Res. 1994, 74, 155-161.
    • (1994) Thromb. Res. , vol.74 , pp. 155-161
    • Uchiba, M.1    Okajima, K.2    Abe, H.3    Okabe, H.4    Takatsuki, K.5
  • 31
    • 0027182009 scopus 로고
    • Synthetic substrates for human Factor VIIa and Factor VIIa-tissue Factor
    • Butenas, S.; Ribarik, N.; Mann, K. G. Synthetic substrates for human Factor VIIa and Factor VIIa-tissue Factor. Biochemistry 1993, 32, 6531-6438.
    • (1993) Biochemistry , vol.32 , pp. 6531-6438
    • Butenas, S.1    Ribarik, N.2    Mann, K.G.3
  • 32
    • 0019809278 scopus 로고
    • Inhibition of activated Factors II, VII, IX, and X by synthetic organic compounds directed against the active-site seryl residue
    • Van der Woerd-De Lange, J. A.; Van Dam-Mieras, M. C. E.; Hemker, H. C. Inhibition of activated Factors II, VII, IX, and X by synthetic organic compounds directed against the active-site seryl residue. Haemostasis 1981, 10, 315-47.
    • (1981) Haemostasis , vol.10 , pp. 315-347
    • Van der Woerd-De Lange, J.A.1    Van Dam-Mieras, M.C.E.2    Hemker, H.C.3
  • 33
    • 0037541104 scopus 로고    scopus 로고
    • Pharmacological intervention at disparate sites in the coagulation cascade: Comparison of anti-thrombotic efficacy vs bleeding propensity in a rat model of acute arterial thrombosis
    • Szalony, J. A.; Taite, B. B.; Girard, T. J.; Nicholson, N. S.; Lachance, R. M. Pharmacological intervention at disparate sites in the coagulation cascade: Comparison of anti-thrombotic efficacy vs bleeding propensity in a rat model of acute arterial thrombosis. J. Thromb. Thrombolysis 2003, 14, 113-121.
    • (2003) J. Thromb. Thrombolysis , vol.14 , pp. 113-121
    • Szalony, J.A.1    Taite, B.B.2    Girard, T.J.3    Nicholson, N.S.4    Lachance, R.M.5
  • 34
    • 0034711777 scopus 로고    scopus 로고
    • Thromboresistance of balloon-injured porcine carotid arteries after local gene transfer of human tissue factor pathway inhibitor
    • Zoldhelyi, P.; McNatt, J.; Shelat, H. S.; Yamamoto, Y.; Chen, Z.-Q.; Willerson, J. T. Thromboresistance of balloon-injured porcine carotid arteries after local gene transfer of human tissue factor pathway inhibitor. Circulation 2000, 101, 289-295.
    • (2000) Circulation , vol.101 , pp. 289-295
    • Zoldhelyi, P.1    McNatt, J.2    Shelat, H.S.3    Yamamoto, Y.4    Chen, Z.-Q.5    Willerson, J.T.6
  • 35
    • 0030824413 scopus 로고    scopus 로고
    • Dissociation of antithrombotic effect and bleeding time prolongation in rabbits by inhibiting tissue factor function
    • Himber, J.; Kirchhofer, D.; Riedereer, M.; Tschopp, T. B.; Steiner, B.; Roux, S. P. Dissociation of antithrombotic effect and bleeding time prolongation in rabbits by inhibiting tissue factor function. Thromb. Haemost. 1997, 7, 1142-1149.
    • (1997) Thromb. Haemost. , vol.7 , pp. 1142-1149
    • Himber, J.1    Kirchhofer, D.2    Riedereer, M.3    Tschopp, T.B.4    Steiner, B.5    Roux, S.P.6
  • 36
    • 0029984412 scopus 로고    scopus 로고
    • Antithrombotic and antilesion benefits without hemorrhagic risks by inhibiting tissue factor pathway
    • Harker, L. A.; Hanson, S. R.; Wilcox, J. N.; Kelly, A. B. Antithrombotic and antilesion benefits without hemorrhagic risks by inhibiting tissue factor pathway. Haemostasis 1996, 26 (suppl 1), 76-82.
    • (1996) Haemostasis , vol.26 , Issue.SUPPL. 1 , pp. 76-82
    • Harker, L.A.1    Hanson, S.R.2    Wilcox, J.N.3    Kelly, A.B.4
  • 39
    • 0041932150 scopus 로고    scopus 로고
    • Pharmacological interruption of acute thrombus formation with minimal hemorrhagic complications by a small molecule tissue Factor/Factor VIIa inhibitor: Comparison to Factor Xa and thrombin inhibition in a nonhuman primate thrombosis model
    • in press
    • Suleymanov, O. D.; Szalony, J. A.; Salyers, A. K.; Lachance, R. M.; Parlow, J. J.; South, M. S.; Wood, R. S.; Nicholson, N. S. Pharmacological interruption of acute thrombus formation with minimal hemorrhagic complications by a small molecule tissue Factor/Factor VIIa inhibitor: Comparison to Factor Xa and thrombin inhibition in a nonhuman primate thrombosis model. J. Pharmacol. Exp. Ther. 2003, in press.
    • (2003) J. Pharmacol. Exp. Ther.
    • Suleymanov, O.D.1    Szalony, J.A.2    Salyers, A.K.3    Lachance, R.M.4    Parlow, J.J.5    South, M.S.6    Wood, R.S.7    Nicholson, N.S.8
  • 43
    • 0032721393 scopus 로고    scopus 로고
    • Crystal structure of active site-inhibited human coagulation Factor VIIa (des-Gla)
    • Kemball-Cook, G. J.; Daniel, J. D.; Tuddenham, E. G. D.; Harlos, K. Crystal structure of active site-inhibited human coagulation Factor VIIa (des-Gla). J. Struct. Biol. 1999, 127, 213-223.
    • (1999) J. Struct. Biol. , vol.127 , pp. 213-223
    • Kemball-Cook, G.J.1    Daniel, J.D.2    Tuddenham, E.G.D.3    Harlos, K.4
  • 45
    • 0032976044 scopus 로고    scopus 로고
    • Probing the structural changes in the light chain of human coagulation Factor VIIa due to tissue factor association
    • Perera, L.; Darden, T. A.; Pedersen, L. G. Probing the structural changes in the light chain of human coagulation Factor VIIa due to tissue factor association. Biophys. J. 1999, 77, 99-113.
    • (1999) Biophys. J. , vol.77 , pp. 99-113
    • Perera, L.1    Darden, T.A.2    Pedersen, L.G.3
  • 47
    • 0030013427 scopus 로고    scopus 로고
    • Molecular interactions of thrombin
    • Tulinsky, A. Molecular Interactions of Thrombin. Semin. Thromb. Hemost. 1996, 117-124.
    • (1996) Semin. Thromb. Hemost. , pp. 117-124
    • Tulinsky, A.1
  • 48
    • 0028912561 scopus 로고
    • The clot thickens: Clues provided by thrombin structure
    • Stubbs, M. T.; Bode, W. The clot thickens: clues provided by thrombin structure. Trends Biochem. Sci. 1995, 20, 23-28.
    • (1995) Trends Biochem. Sci. , vol.20 , pp. 23-28
    • Stubbs, M.T.1    Bode, W.2
  • 49
    • 0034680369 scopus 로고    scopus 로고
    • Preparation, characterization, and the crystal structure of the inhibitor ZK-807834 (CI-1031) complexed with Factor Xa
    • Adler, M.; Davey, D. D.; Phillips, G. B.; Kim, S. H.; Jancarik, J.; Rumennik, G.; Light, D. R.; Whitlow, M. Preparation, characterization, and the crystal structure of the inhibitor ZK-807834 (CI-1031) complexed with Factor Xa. Biochemistry 2000, 39, 12534-12542.
    • (2000) Biochemistry , vol.39 , pp. 12534-12542
    • Adler, M.1    Davey, D.D.2    Phillips, G.B.3    Kim, S.H.4    Jancarik, J.5    Rumennik, G.6    Light, D.R.7    Whitlow, M.8
  • 53
    • 0029923976 scopus 로고    scopus 로고
    • X-ray structure of active site-inhibited clotting Factor Xa. Implications for drug design and substrate recognition
    • Brandstetter, H.; Kuhne, A.; Bode, W.; Huber, R.; von der Saal, W.; Wirthensohn, K.; Engh, R. A. X-ray structure of active site-inhibited clotting Factor Xa. Implications for drug design and substrate recognition. J. Biol. Chem. 1996, 271, 29988-29992.
    • (1996) J. Biol. Chem. , vol.271 , pp. 29988-29992
    • Brandstetter, H.1    Kuhne, A.2    Bode, W.3    Huber, R.4    Von der Saal, W.5    Wirthensohn, K.6    Engh, R.A.7
  • 55
    • 0037330483 scopus 로고    scopus 로고
    • Metabolic activation of a pyrazinone-containing thrombin inhibitor, evidence for novel biotransformation involving pyrazinone ring oxidation, rearrangement, and covalent binding to proteins
    • Singh, R.; Silva Elipe, M. V.; Pearson, P. G.; Arison, B. H.; Wong, B. K.; White, R.; Yu, X. O.; Burgey, C. S.; Lin, J. H.; Baillie, T. A. Metabolic activation of a pyrazinone-containing thrombin inhibitor, evidence for novel biotransformation involving pyrazinone ring oxidation, rearrangement, and covalent binding to proteins. Chem. Res. Toxicol. 2003, 16, 198-207.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 198-207
    • Singh, R.1    Silva Elipe, M.V.2    Pearson, P.G.3    Arison, B.H.4    Wong, B.K.5    White, R.6    Yu, X.O.7    Burgey, C.S.8    Lin, J.H.9    Baillie, T.A.10
  • 60
    • 0037029827 scopus 로고    scopus 로고
    • Synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic ester, a new conformationally constrained peptidomimetic derivative
    • Gloanec, P.; Herve, Y.; Bremand, N.; Lecouve, J.; Breard, F.; De Nanteuil, G. Synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic ester, a new conformationally constrained peptidomimetic derivative. Tetrahedron Lett. 2002, 43, 3499-3501.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3499-3501
    • Gloanec, P.1    Herve, Y.2    Bremand, N.3    Lecouve, J.4    Breard, F.5    De Nanteuil, G.6
  • 62
    • 0033152131 scopus 로고    scopus 로고
    • Solution-phase chemical library synthesis using polymer-assisted purification techniques
    • Parlow, J. J.; Devraj, R. V.; South, M. S. Solution-phase chemical library synthesis using polymer-assisted purification techniques. Curr. Opin. Chem. Biol. 1999, 3, 320-336.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 320-336
    • Parlow, J.J.1    Devraj, R.V.2    South, M.S.3
  • 64
    • 0032171668 scopus 로고    scopus 로고
    • Studies on the reactions of HOBt, HOOBt, HOSu with dichloroalkane solvents
    • Ji, J.; Zhang, D.; Ye, Y.; Xing, Q. Studies on the reactions of HOBt, HOOBt, HOSu with dichloroalkane solvents. Tetrahedron Lett. 1998, 39, 6515-6516.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6515-6516
    • Ji, J.1    Zhang, D.2    Ye, Y.3    Xing, Q.4
  • 65
    • 0033973716 scopus 로고    scopus 로고
    • Polymer-assisted solution-phase (PASP) library synthesis of α-Ketoamides
    • South, M. S.; Dice, T. A.; Parlow, J. J. Polymer-assisted solution-phase (PASP) library synthesis of α-Ketoamides. Biotechnol. Bioeng. 2000, 61, 51-57.
    • (2000) Biotechnol. Bioeng. , vol.61 , pp. 51-57
    • South, M.S.1    Dice, T.A.2    Parlow, J.J.3
  • 66
    • 0003686469 scopus 로고
    • Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent
    • Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent. J. Org. Chem. 1979, 44, 1247-1251.
    • (1979) J. Org. Chem. , vol.44 , pp. 1247-1251
    • Olah, G.A.1    Narang, S.C.2    Gupta, B.G.B.3    Malhotra, R.4
  • 67
    • 0141698081 scopus 로고    scopus 로고
    • note
    • 50 values.
  • 68
    • 0141809498 scopus 로고    scopus 로고
    • note
    • 1 arginine mimetic amides will be the topic of a future publication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.