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Original Article

Protease Inhibitors: Part 4. Synthesis of Weakly Basic Thrombin Inhibitors Incorporating Pyridinium-Sulfanilylaminoguanidine Moieties

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Pages 335-356 | Received 01 Sep 1999, Published online: 02 Jul 2010

References

  • Patel A., Smith H. J., Stürzebecher J. “Design of enzyme inhibitors as drugs”. Introduction to the Principles of Drug Design and Action, H. J Smith. Harwood Academic Publishers, OPA, Amsterdam 1998; 261–330
  • Shafer J. A. Curr. Opin. Chem. Biol 1998; 2: 458–465
  • Sanderson P. E., Naylor-Olsen A. M. Curr. Med. Chem 1998; 5: 289–304
  • Stürzehecher J., Meier J. J. Enzyme Inhib 1995; 9: 1–2
  • Steimetzer T., Batdorsdhjin M., Kleinwachter P., Seyfarth L., Greiner G., Reissmann S., Stürzehecher J. J. Enz. Inhib 1999; 14: 203–216
  • Stürzehecher J., Prasa D., Hauptmann J., Vieweg H., Wikstrom P. J. Med. Chem 1997; 40: 3091–3099
  • Pavone V., De Simone G., Nastri F., Galdiero S., Staiano N., Lomhardi A., Pedone C. J. Biol. Chem 1998; 379: 987–1006
  • Stone S. R., Le Bonniec B. F. Thrombin. Handbook of Proteolytic Enzymes - CD-ROM, A. J Barrett, N. D Rawlings, J. F Woessner. Academic Press, London 1998, Chapter 55
  • Engh R. A., Brandstetter H., Sucher G., Eichinger A., Baumann U., Bode W., Huber R., Poll T., Rudolph R., von der Saal W. Structure. 1996; 4: 1353–1362
  • Babine R. E., Bender S. L. Chem. Rev. 1997; 97: 1359–1472
  • Salemme F. R., Spurlino J., Bone R. Structure. 1997; 5: 319–324
  • Eriksson U. G., Renherg L., Bredherg U., Teger-Nilsson A. C., Regardh C. G. Biopharm. Drug Dispos. 1998; 19: 55–64
  • Bajusz S., Szell E., Bagdy D., Barhas E., Horvath G., Dioszegi M., Fittler Z., Szabo G., Juhasz A., Tomori E., Szilagyi G. J. Med. Chem 1990; 33: 1729–1735
  • Wienand A., Ehrhardt C., Metternich R., Tapparelli C. Bioorg. Med. Chem 1999; 7: 1295–1307
  • Krishnan R., Zhang E., Hakansson K., Arni R. K., Tulinsky A., Lim-Wilby M. S., Levy O. E., Semple J. E., Brunck T. K. Biochemistry 1998; 37: 12094–13103
  • Claeson G., Philipp M., Agner E., Scully M. F., Metternich R., Kakkar V. V., De T. Soyz, Niu L. H. Biochem. J. 1993; 290: 309–312
  • Stürzehecher J., Prasa D., Bretschneider E., Bode W., Bauer M., Brandstetter H., Wikstrom P., Vieweg H. New developments in the field of henzamidine-derived thrombin inhibitors. DIC - Pathogenesis, Diagnosis, and Therapy of Disseminated Intra-vascular Fibrin Formation, G. Muller-Berghaus, K. Madlener, M. Blomhack, J. W Cate. Excerpta Medica, Amsterdam, London, New York, Tokyo 1993; 183–190
  • Lumma W. C., Witherup K. M., Tucker T. J., Brady S. F., Sisko J. T., Naylor-Olsen A. M., Lewis S. D., Lucas B. J., Vacca J. P. J. Med. Chem. 1998; 41: 1011–1013
  • Semple J. E., Rowley D. C., Brunck T. K., Ha-Uong T., Minami N. K., Owens T. D., Tamura S. Y., Goldman E. A., Siev D. V., Ardecky R. J., Carpenter S. H., Ge Y., Richard B. M., Nolan T. G., Hakanson K., Tulinsky A., Nutt R. F., Ripka W. C. J. Med. Chem. 1996; 39: 4531–4536
  • Sixma J. J., de Groot P. G. Thromb. Res. 1992; 68: 507–512
  • Okamoto S., Kinjo K., Hijkata A., Kikumoto R., Tamao Y., Ohkubo K., Tonomura S. J. Med. Chem. 1980; 23: 827–830
  • Stürzebecher J., Markwardt F., Voigt B., Wagner G., Walsmann P. Thromb. Res. 1983; 29: 635–642
  • Groutas W. C., Kuang R., Venkataraman R., Epp J. B., Ruan S., Prakash O. Biochemistry 1997; 36: 4739–4750
  • Supuran C. T., Scozzafava A., Briganti F., Clare B. W. J. Med. Chem 2000; 43, in press
  • Clare B. W., Scozzafava A., Briganti F., Supuran C. T. J. Enz. Inhib 1999, in press
  • Balaban A. T., Dinculescu A., Dorofeenko G. N., Fischer G. W., Koblik A. V., Mezheritskii V. V., Schroth W. “Pyrylium salts: Syntheses, reactions and physical properties”. Advances in Heterocyclic Chemistry, A. R Katritzky. Academic Press, New York 1982; 8–360
  • Supuran C. T., Pop E., Dinculescu A. Heterocycles. 1994; 37: 667–671
  • Neidlein R., Witerzens P. Monats. Chem. 1975; 106: 643–648
  • Supuran C. T., Clare B. W. Eur. J. Med. Chem. 1995; 30: 687–696
  • Lottenberg R., Christensen U., Jackson C. M., Coleman P. L. Meth. Enzymol. 1981; 80: 341–361
  • Hemker H. C., Willems G. M., Beguin S. A. Thromb. Huemostas. 1986; 56: 9–17
  • Bell P. H., Roblin R. O. J. Am. Chem. Soc. 1942; 64: 2905–2917
  • Supuran C. T., Manole G., Dinculescu A., Schiketanz A., Gheorghiu M. D., Puscas I., Balaban A. T. J. Pharm. Sci. 1992; 81: 716–719
  • Supuran C. T., Scozzafava A., Ilies M. A., Iorga B., Cristea T., Chiraleu F., Banciu M. D. Eur. J. Med. Chem. 1998; 33: 577–594
  • Anderson G. W., Zimmerman J. E., Callahan F. M. J. Am. Chem. Soc 1963; 85: 3039
  • Sheehan J. C., Ledis S. L. J. Am. Chem. Soc 1973; 95: 875–879
  • Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G., Supuran C. T. J. Med. Chem 1999; 42: 2641–2650
  • Supuran C. T., Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G. Eur. J. Pharm. Sci 1999; 8: 317–328
  • Scozzafava A., Briganti F., Mincione G., Menabuoni L., Mincione F., Supuran C. T. J. Med. Chem 1999; 42: 3690–3700
  • Banner D. W., Hadvary P. J. Biol. Chem 1991; 266: 20085–20093
  • Balaban A. T., Toma C. Tetrahedron Suppl. 1966; 7: 1–7
  • Dinculescu A., Balaban A. T. Rev. Roum. Chim. 1980; 25: 1505–1528
  • Supuran C. T., Banciu M. D., Balaban A. T. Rev. Roum. Chim. 1993; 38: 199–205
  • Bode W., Turk D., Karshikov A. Protein Sci. 1992; 1: 426–471
  • Stubbs M. T., Bode W. Thromb. Res. 1993; 69: 1–58

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