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Syntezy wybranych leków pochodnych 2-amino-1H-benzimidazolu

Treść / Zawartość
Identyfikatory
Warianty tytułu
EN
Synthesis of Selected drugs 2-amino-1H-benzimidazole derivatives
Języki publikacji
PL
Abstrakty
EN
2-Amino-1H-benzimidazole fragment occurs in broad spectrum of drugs with anticancer, antiviral, antifungal, anthelmintic and antihistamine properties. There are 30 drugs, 2-amino-1H-benzimidazole derivatives, registered in the world. Mebendazole, Albendazole and another derivatives are antihelmintic drugs which are believed to work by selectively inhibiting the synthesis of microtubules in parasitic worms, and by destroying extant cytoplasmic microtubes in their intestinal [9, 12, 14]. Astemizole was a second-generation antihistamine drug that has a long duration of action. It has been withdrawn from the market in most countries because of rare but potentially fatal side effects [19]. Mizolastine is non-sedating antihistamine drug [21]. It blocks H1 receptors and doesn’t prevent the actual release of histamine from mast cells, but just prevents it binding to receptors. Enviroksim and its isomer Zinviroksim and Enviraden are antivirial drugs [26, 27]. They inhibit multiplication of 15 different serotypes of rhinovirus. Benomyl is a systemic fungicide that is selectively toxic to microorganisms [29]. Benomyl binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation. Carbendazim is a widely used, broad-spectrum fungicide and a metabolite of Benomyl [29]. It’s also shown an anticancer activity. Oncodazole shows antifungal, antineoplastic and antihelmintic activities, which exerts its effect in cells by binding to tubulin and interfering with the polymerization of microtubules [33].
Rocznik
Strony
695--714
Opis fizyczny
Bibliogr. 34 poz., schem.
Twórcy
autor
  • Katedra i Zakład Technologii Leków Uniwersytet Medyczny im Piastów Śląskich we Wrocławiu pl. Nankiera 1, 50-140 Wrocław
  • Katedra i Zakład Technologii Leków Uniwersytet Medyczny im Piastów Śląskich we Wrocławiu pl. Nankiera 1, 50-140 Wrocław
Bibliografia
  • [1] W. Nawrocka, B. Sztuba, H. Liszkiewicz, M.W. Kowalska, J. Wietrzyk, D. Nevozhai, A. Opolski, Polish J. Chem., 2005, 79, 709.
  • [2] W. Nawrocka, M. Zimecki, T. Kuznicki, M.W. Kowalska, Arch. Pharm. Pharm. Med. Chem., 1999, 332, 85.
  • [3] W. Nawrocka, B. Sztuba, M.W. Kowalska, H. Liszkiewicz, J. Wietrzyk, A. Nasulewicz, M. Peczyska, A. Opolski, Il Farmaco, 2004, 59, 83.
  • [4] W. Nawrocka, B. Sztuba, A. Dry, J. Wietrzyk, J. Kosendiak, A. Opolski, Polish J. Chem., 2006, 80, 279.
  • [5] W.P. Nawrocka, A. Nowicka, H. Liszkiewicz, Wiad. Chem., 2012, 66, 811.
  • [6] W.P. Nawrocka, A. Nowicka, H. Liszkiewicz, Wiad. Chem., 2012, 66, 839.
  • [7] W.P. Nawrocka, A. Nowicka, Wiad. Chem., 2013, 67, 715.
  • [8] G . Virella, Mikrobiologia i choroby zakane, Wydawnictwo Medyczne Urban & Partner, Wrocaw 2000.
  • [9] E .C. Wagner, W.H. Millert, Org. Syntheses Col., 1943, 2, 66.
  • [10] J. Van Gelder, A. Raeymaekers, L. Roves, RFN 2029627, 1971, C.A. 1971, 74, 100047a.
  • [11] N . Negwer, Organic Chemical Drugs and Their Synonyms, Akademie Verlag, Berlin 1987.
  • [12] P. Piccardi, G. Confalonieri, P.G. Ramella, U.S. Patent 4,182,893, 1980.
  • [13] L .B. Townsend, D.S. Wise, Parasitology Today, 1990, 6, 107.
  • [14] R .J. Gyurik, V.J. Theodorides, U.S. Patent 3,915,986, 1975; V.J. Theodorides, R.J. Gyurik, W.D. Kinsbury, R.C. Parish, Experientia, 1976, 32, 702; 14a. M.H. Pourgholami, L. Woon, R. Almajd, J. Akhter, P. Bowery, D.L. Morris, Cancer Lett., 2001, 165, 43.
  • [15] A . Li, Z. Hu, Chinese Journal of Pharmaceuticals, 1992, 23, 385.
  • [16] A . Zejc, M. Gorczyca, Chemia leków, Wydawnictwo lekarskie PZWL, Warszawa 2008.
  • [17] R . Iemura, T. Kawashima, T. Fukuda, K. Ito, G. Tsukamoto, J. Med. Chem, 1986, 29, 1178.
  • [18] A . Orjales-Venero, N. Garcia-Dominquez, V. Rubio-Royo, R. Rodes-Solanes, U.S. Patent 5,256,665, 1993.
  • [19] F . Janssens, R. Stokbroekx, J. Torremans, M. Luyckx, U.S. Patent 4,219,559, 1980.
  • [20] K. Falek, A. Tyrala, PL. 162,730, 1994.
  • [21] P. Rosenzweig, J.J. Thebault, H. Caplain, C. Dubruc, G. Bianchetti, E. Fuseau, P.L. Morselli, Ann Allergy, 1992, 69, 135.
  • [22] M.J. Fischer, J.J. Paulussen, J.A. Kok-Van Esterik, V.S. Van der Heijden, N.J. De Mol, L.H. Janssen, Eur. J. Pharmacol., 1997, 322, 97.
  • [23] P. Manoury, J. Binet, G. Defosse, U.S. Patent 4,820,710, 1989.
  • [24] M.L. Zaremba, J. Borowski, Mikrobiologia lekarska, Wydawnictwo Lekarskie PZWL, Warszawa 2004.
  • [25] M.J. Tebbe, W.A. Spitzer, F. Victor, S.C. Miller, C.C. Lee, T.R. Sattelberg Sr., E. McKinney, J.C. Tang, J. Med. Chem., 1997, 40, 3937.
  • [26] J.H. Wikel, C.J. Paget, D.C. DeLong, J.D. Nelson, C.Y.E. Wu, J.W. Paschal, A. Dinner, R.J. Templeton, M.O. Chaney, N.D. Jones, J.W. Chamberlin, J. Med. Chem., 1980, 23, 386.
  • [27] F . Victor, T.J. Brown, K. Campanale, B.A. Heinz, L.A. Shipley, K.S. Su, J. Tang, L.M. Vance, W.A. Spitzer, J. Med. Chem., 1997, 40, 1511.
  • [28] L . Jia, H. Wong, Y. Wang, M. Garza, S.D. Weitman, Journal of Pharmaceutical Sciences, 2003, 92, 161.
  • [29] H .M. Loux, U.S. Patent 3,010,968, 1961.
  • [30] H .L. Klopping, U.S. Patent 3,631,176, 1971.
  • [31] M. Lezcano, W. Al-Soufi, M. Novo, E. Rodriguez-Nunez, J. Vazquez Tato, J.Agric. Food Chem., 2002, 50, 108.
  • [32] L .A. Hammond, K. Davidson, R. Lawrence, J.B. Camden, D.D. Von Hoff, S. Weitman, E. Izbicka, J. Cancer Res. Clin. Oncol., 2001, 127, 301.
  • [33] J. Van Gelder, L.F.C. Roevens, L.H. Belgians, A.H.M. Rayemaekers, U.S. Patent 3,657,267, 1972.
  • [34] L .I. Kruse, D.L. Ladd, P.B. Harrsch, F.L. McCabe, S.M. Mong, L. Faucette, R. Johnson, J. Med. Chem., 1989, 32, 409.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-b5cdb61d-fa5a-4011-bc35-ca8772749ada
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