Syntezy, struktury i aktywność biologiczna pochodnych imidazo[4,5-b] pirydyny. Część 1

• Autorzy: Liszkiewicz H. , Nowicka A. , Nawrocka W. P.

Warianty tytułu

EN

Synthesis, structures and biological activity of imidazo [4,5-b]pyridine derivatives. Part 1

• Języki publikacji: PL

Abstrakty

EN

This review presents most of the literature data about imidazo[4,5-b]pyridine derivatives and their biological activity. The main goal of this paper is to present various methods for the preparation of imidazo[4,5-b]pyridine analogues. There are some drugs, imidazo[4,5-b]pyridine derivatives, registered in the world, which exhibit diverse pharmacological activities. Noberastine [4] represent antihistaminic II generation drug with selective activity to H1 receptors. Tenatoprazole [5] is a novel proton pump inhibitor with a prolonged plasma half-life which possesses antiulcer activity. Sulmazole [3] is a new cardiotonic agent, an A1 adenosine receptor antagonist. Based on the review of the chemical literature, derivatives of imidazole[4,5-b] pyridine showed a multipharmacological effects. Presented compounds exhibit anticancer [14, 17, 19], antidepressant [44, 45], cardiotonic, anticoagulant [37] activities. Some of them can be used in the treatment of heart diseases [3]. There were also described derivatives of imidazo[4,5-b]pyridine with the potential use in the treatment of diabetes [48], hypertension and hyperlipidemia. Some chemical compounds which contain in their structure the imidazo[4,5-b]pyridine system inhibit neurodegeneration [34, 38] and can be used in the treatment of neurodegenerative disorders eg. Parkinson’s disease, Alzheimer’s disease or multiple sclerosis. In addition, some of the imidazo[4,5-b]pyridine possess antivirial [40–42], antimicrobial and cytotoxic activities.

Słowa kluczowe

PL

pochodne imidazo[4,5-b]pirydyny; aktywność biologiczna; synteza; struktura

EN

imidazo[4,5-b]pyridine derivatives; biological activity; synthesis; structure

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2012
• Tom: [Z] 66, 11-12
• Strony: 1071--1095
• Opis fizyczny: Bibliogr. 48 poz., schem.

Twórcy

autor

Liszkiewicz H.

autor

Nowicka A.

autor

Nawrocka W. P.

• Katedra i Zakład Technologii Leków Uniwersytet Medyczny im Piastów Śląskich we Wrocławiu pl. Nankiera 1, 50-140 Wrocław,

Bibliografia

• [1] W.J. Parsons, V. Ramkumar, G.L. Stiles, Mol. Pharmacy., 1988, 33, 441.
• [2] M. Zając, E. Pawełczyk, A. Jelińska, Chemia leków, Wydawnictwo Naukowe Akademii Medycznej w Poznaniu, 2006.
• [3] P. Barraclough, J.W. Black, D. Cambridge, D. Collard, D. Firmin, V.P. Gerskowitch, R.C. Glen, H. Giles, A.P. Hill, R.A.D. Hull, R. Iyer, W.R. King, C.O.Kneen, J.C. Lindon, M.S. Nobbs, P. Randall, G.P.Shah, S. Smith, S.J. Vine, M.V. Whiting, J.M. Williams, J. Med. Chem. 1990, 33, 2231.
• [4] M.M.L. Janssens, P.H. Howarth, Clin. Rev. Allergy, 1993, 11, 111.
• [5] N. Matsuishi, H. Takeda, K. Iizumi, K. Murakami, A. Hisamitsu, patent US 4808596; www.ip.com (accessed 10.03 2012).
• [6] Y. Mao, X. Zhang, L. Li, B. Yuan, G. Lu, Regul. Toxicol. Pharmacol., 2008, 50, 75.
• [7] J.P. Galmiche, S. Bruley Des Varannes, P. Ducrott , S. Sacher-Huvelin, F. Vavasseur, A. Taccoen, P. Fiorentini, M. Homerin, Aliment Pharmacol. Ther., 2004, 19, 655.
• [8] S. Sripathi, R.R. Bojja, V.R. Karnati, V.V.N.K.V. Prasada Raju, M.D. Khunt, Org. Process Res. Dev., 2009, 13, 804.
• [9] S. Piras, M. Loriga, G. Paglietti, Il Farmaco, 1993, 48, 1249.
• [10] P.J. Zimmermann, Ch. Brehm, A. Palmer, M.V. Chiesa, W.A. Simmon, S. Postius, W. Kromer, E. Sturm, W. Buhr, WO 2005/123730, 2005, CA. 144, 88289.
• [11] F.E. Janssens, J.E.G. Guillemont, F.M. Sommen, J.F. Bonfanti, WO 2008/090200, CA: 2008, 149, 200952.
• [12] H .Y. Yoo, K.J. Chung, M.S. Chang, S.G. Kim, W.S. Choi, D P. Kang, J.M. Lee, J.H. Paek, K.B. Kim, S.H. Park, Y.H. Kim, K.H. Seo, patent WO/1997/003077, www.ip.com (accessed 21.04. 2012).
• [13] W. Janiec, Farmakodynamika, Wydawnictwo Lekarskie PZWL, 2008.
• [14] H . Graboyes, A.R. Day, J. Am. Chem. Soc., 1957, 79, 6421.
• [15] T. Itoh, K. Ono, T. Sugawara, Y. Mizuno, J. Heterocycl. Chem., 1982, 19, 513.
• [16] P. Lan, W.N. Chen, W.M. Chen, Eur. J. Med. Chem., 2011, 46, 77.
• [17] V. Bavetsias, C. Sun, N. Bouloc, J. Reynisson, P. Workman, S. Linardopoulos, E. MacDonald, Bioorg. Med. Chem. Lett., 2007, 17, 6567.
• [18] V. Bavetsias, J.M. Large, C. Sun, N. Bouloc, M. Kosmopoulou, M. Matteucci, N.E. Wilsher, V. Martins, J. Reynisson, B. Atrash, A. Faisal, F. Urban, M. Valenti, J. Med. Chem., 2010, 53, 5213.
• [19] I. Gillerman, B. Fischer, J. Med. Chem. 2011, 54, 107.
• [20] G. Cristalli, S. Costanzi, C. Lambertucci, G. Lupidi, S. Vittori, R. Volpini, E. Camaioni, Med. Res. Rev., 2001, 21, 105.
• [21] S. Mylonas, A.Mamalis, J. Heterocycl. Chem., 2005, 42, 1273.
• [22] C. Temple Jr, B.H. Smith, R.D. Elliott, J.A. Montgomery, J. Med. Chem., 1973, 16, 292.
• [23] A.K. Singh, J.W. Lown, Synth. Commun., 1998, 28, 4059.
• [24] A.K. Singh, J.W. Lown, Synth. Commun, 2000, 30, 923.
• [25] H . Liszkiewicz, M.W. Kowalska, W. Nawrocka, A. Wójcicka, J. Wietrzyk, A. Nasulewicz, M. Pełczyńska, A. Opolski, Phosphorus, Sulfur Silicon Relat. Elem., 2003, 12, 2725.
• [26] H . Liszkiewicz, W.P. Nawrocka, B. Sztuba, J. Wietrzyk, J. Jaroszewicz, A. Nasulewicz, M. Pełczyńska, Acta Pol Pharm., 2011, 68, 349.
• [27] F. Sączewski, A. Stencel, A.M. Bieńczak, K.A. Langowska, M. Michaelis, W. Werel, R. Hałasa, P. Reszka, P.J. Bednarski, Eur. J. Med. Chem., 2008, 43, 1847
• [28] A. Kaźmierczuk, Z.M. Kiliańska, Postepy Hig. Med. Dosw., 2009, 63, 502.
• [29] Y.L. Janin, Drug Discovery Today, 2010, 15, 342.
• [30] M. Hranjec, B. Lučić, I. Ratkaj, S.K. Pavelić, I. Piantanida, K. Pavelić, G. Karminski-Zamola, Eur. J. Med. Chem., 2011, 46, 2748.
• [31] P.T. Wan, M.J. Garnett, S.M. Roe, S. Lee, D. Niculescu-Duvaz, V.M. Good, C.M. Jones, C.J. Marshall, et al., Cell, 2004, 116, 855.
• [32] D. Niculescu-Duvaz, C. Gaulon, H. Dijkstra, I. Niculescu-Duvaz, A. Zambon, D. Menard, B.M.J.M. Suijkerbuijk, A. Nourry, L. Davies, H. Manne, F. Friedlos, L. Ogilvie, D. Hadley, S. Whittaker, R. Kirk, A. Gill, et al., J. Med. Chem., 2009, 52, 2255.
• [34] D. Turzyńska, A. Skórzewska, A. Sobolewska, A. Płażnik, Postępy Psychiatrii i Neurologii, 2005, 14, 1.
• [35] B .F. McGiunness, A.G. Cole, G. Dong, M.R. Brescia, Y. Shao, I. Henderson, P.G. Wines, E. Quadros, Bioorg. Med. Chem. Lett., 2010, 20, 6845.
• [36] K. Nakajima, S. Kohsaka, Neurosci. Res., 1993, 17, 187.
• [37] J. Ock, S. Kim, K.Y Yi, N.J. Kim, H.S. Han, Biochem. Pharmacol., 2010, 79, 596.
• [38] G.V. Rayasam, Br. J. Pharmacol., 2009, 156, 885.
• [39] P.I. Arvidsson, E. Arzel, J. Burrows, M. Claesson, C. Ray, T. Rein, D. Rotticci, P. Soederman, WO 2007/040438, 2007, www.ip.com.
• [40] R. Giraudon, G. Santini, patent US 4579853, www.ip.com (accessed 30.04 2012).
• [41] B .R.R. Kesteleyn, W.B.G. Schepens, K.I.E, Amssoms, WO 2007/113290, 2007, www.ip.com.
• [42] D. Kim, L. Wang, J.J. Hale, Ch.L. Lynch, R.J. Budhu, M. MacCoss, S.G. Mills, L. Malkowitz, S.L Gould., J.A. DeMartino, M.S. Springer, D. Hazuda, M. Miller, J. Kessler, R.C. Hrin, G. Carver, A. Carella, K. Henry, J. Lineberhger, W.A. Schleif, E.A. Emini, Bioorg. Med. Chem. Lett., 2005, 15, 2129.
• [42] D.J. Cundy, G. Holan, M. Otaegui, G.W. Simpson, Bioorg. Med. Chem. Lett., 1997, 7, 669; J.L. Anderson, J.F. Carlquist, J.B. muhlestein, et. Al., J. Am. Coll. Cardiol., 1998, 32, 35.
• [43] A.G. Arvanitis, J.T. Rescinito, C.R. Arnold, R.G. Wilde, G.A. Cain, J.H. Sun, Jia-Sheng Yan, C.A. Teleha, L.W. Fitzgerald, J. McErloy, R. Zaczek, P.R. Hartig, S. Grossman, S.P. Arneric, P.J. Gilligan, R.E. Olson, D.W. Robertson, Bioorg. Med. Chem. Lett., 2003, 13, 125.
• [44] W. Kostowski, Z.S. Herman, Farmakologia, Podstawy farmakoterapii, Wyd. PZWL, 2005, Wyd. III, Tom I-II.
• [45] L. Zhang, M.A. Brodney, J. Candler, A.C. Doran, A.J. Duplantier, I.V. Efremov, E. Evrard, K. Kraus, A.H. Ganong, J.A. Haas, A.N. Hanks, K. Jenza, J.T. Lazzaro, N. Maklad, S.A. McCarthy, W. Qian, B.N. Rogers, M.D. Rottas, C.J. Schmidt, J.A. Siuciak, F.D. Tingley, A.Q Zhang, J. Med. Chem., 2011, 54, 1724.
• [46] R. Giani, patent EP 0397615 A3, www.ip.com (accessed 22.03 2012).
• [47] E. Nicolai, J. Goyard, T. Benchetrit, J.M. Teulon, F. Caussade, A. Virone, Ch. Delchambre, A. Cloarec, J. Med. Chem., 1993, 36, 1175.
• [48] M. Oguchi, K. Wada, H. Honma, A. Tanaka, T. Kaneko, S. Sakakibara, J. Ohsumi, N. Serizawa, T. Fujiwara, H. Horikoshi, T. Fujita, J. Med. Chem. 2000, 43, 3052.