Identyfikatory
Warianty tytułu
Synthesis and biological activity of pyrrolo[3,4-c]pyridine derivatives
Języki publikacji
Abstrakty
Pyrrolo[3,4-c]pyridine is one of the six structural isomers of the bicyclic ring system containing pyrrole moiety condensed with a pyridine nucleus. This review presents most of the literature data about synthetic pyrrolo[3,4-c]pyridine derivatives and their biological activity. S. Gabriel and J. Colman [4] discovered this isomer for the first time and named it “merimine” [Fig. 3]. The main goal of this study is the presentation of various methods for the preparation of pyrrolo[3,4-c]pyridine derivatives. Compounds containing the pyrrolo[3,4-c]pyridine scaffold can be synthesized from different substrates, but the syntheses may be classified into two main categories: annulation of pyrrole ring onto pyridine derivatives or annulation of pyridine ring onto pyrrole derivatives. Biological investigations have shown that pyrrolo[3,4-c]pyridine derivatives have a wide spectrum of actions. Most of them have been studied as analgesic and sedative agents [35–40]. Antitumor [19, 42, 45], antiviral [27], antituberculostatic [43] activities have been found. Pyrrolo[3,4-c]pyridine derivatives can also be used in the treatment of nervous [20, 41] and immune [19, 42] system diseases.
Wydawca
Czasopismo
Rocznik
Tom
Strony
251--276
Opis fizyczny
Bibliogr. 45 poz., schem.
Twórcy
autor
- Katedra i Zakład Technologii Leków, Uniwersytet Medyczny im. Piastów Śląskich we Wrocławiu, pl. Nankiera 1, 50-140 Wrocław
Bibliografia
- [1] Y . Kawato, H. Terasawa, Prog. Med. Chem., 1997, 34, 69.
- [2] M . Kitajima, S. Yoshida, K. Yamagata, M. Nakamura, H. Takayama, K. Saito, H. Seki, N. Aimi, Tetrahedron, 2002, 58, 9169.
- [3] T .R. Govindachari, K.R. Ravindranath, N. Viswanathan, J. Chem. Soc. Perkin Trans. 1, 1974, 1215.
- [4] S. Gabriel, J. Colman, Ber., 1902, 35, 2832.
- [5] H . Strache, Monatsh. fur Chem. 1890, 11, 142.
- [6] H .H. Fox, J. Org. Chem., 1952, 17, 547.
- [7] A . da Settimo, G. Primofiore, F. da Settimo, F. Simorini, C. LaMotta, A. Martinelli, E. Boldrini, Eur. J. Med. Chem., 1996, 31, 49.
- [8] S.M. Gadekar, J.L. Frederick, J. Semb, J. Vaughan, J. Org. Chem., 1961, 26, 468.
- [9] J. Cobo, A. Sanchez, M. Nogueras, Tetrahedron, 1997, 53, 8225.
- [10] N .M. Nascimento Jr., T.C. Mendes, D.M. Leal, C.M. Correa, R.T. Sudo, G. Zapata-sudo, E.J. Barreiro, C.A. Fraga, Bioorg. Med. Chem. Lett., 2010, 20, 74.
- [11] E . Meredith, K. Beattie, R. Burgis, M. Capparelli, J. Chapo, L. DiPietro, G. Gamber, I. Enyedy, D.B. Hood, V. Hosagrahara, Ch. Jewell, K.A. Koch, W. Lee, O. Rozhitskaya, N. Soldermann, C. Springer, M. van Eis, R.B. Vega, W. Yan, Q. Zhu, L.G. Monovich, J. Med. Chem., 2010, 53, 5422.
- [12] Y . Oka, K. Itoh, A. Miyake, N. Tada, K. Omura, M. Tomimoto,S. Yurugi, Chem. Pharm. Bull., 1975, 23, 2306.
- [13] A .N. Vasiliev, Y.S. Kayukov, A.N. Lyshchikov, O.E. Nasakin, O.V. Kayukova, Chem. Heterocycl. Comp., 2003, 39, 1182.
- [14] A .N. Vasiliev, A.N. Lyshchikov, O.E. Nasakin, Y.S. Kayukov, Chem. Heterocycl. Comp., 2004, 40, 460.
- [15] R .G. Jones, J. Am. Chem. Soc., 1951, 72, 5610.
- [16] V .N. Maksimova, O.V. Ershov, K.V. Lipin, A.V. Eremkin, O.E. Nasakin, J. Org. Chem., 2012, 48, 426.
- [17] A . Wang, S. Tandel, H. Zhang, Y. Huang, T.C. Holdeman, E. Biehl, Tetrahedron, 1998, 54, 3391.
- [18] T . Delaine, V. Bernardes-Genisson, B. Meunier, J. Bernardou, J. Org. Chem., 2007, 72, 675.
- [19] Y . Arikawa, Q. Dong, V. Feher, B. Jones, B. Lam, Z. Nie, C. Smith, M. Takahashi, U.S.Pat. Appl. Publ., 2011, WO 2011/079051 A1 20110623,46.
- [20] J. Kossakowski, T. Zawadowski, Acta Pol. Pharm., 1995, 52, 245.
- [21] I . Ahmed, G.W.H. Cheeseman, B. Jaques, Tetrahedron, 1979, 35, 1145.
- [22] O . Mumm, O. Bohme, Chem. Ber., 1921, 54, 730.
- [23] E . Wagner, A. Wojcicka, I. Bryndal, T. Lis, Polish J. Chem., 2009, 83, 207.
- [24] K.R. Shah, C.D. Blanton Jr, J. Org. Chem., 1982, 47, 502.
- [25] J. Cobo, A. Sanchez, M. Nogueras, Tetrahedron, 1998, 54, 5753.
- [26] A . Budzowski, M. Pitak, K. Stadnicka, Monat. Chem., 2007, 138, 1257.
- [27] X.Z. Zhao, K. Maddali, M. Metifiot, S.J. Smith, S.C. Vu, C. Marchand, S.H. Hughes, Y. Pommier, T. Burke Jr., Chem. Biol. Drug. Des., 2012, 79, 157.
- [28] W . Malinka, T. Bodalski, Pol. J. Chem., 1995, 69, 95.
- [29] K.J. Buysens, D.M. Vandenberghe, G.J. Hoornaert, Tetrahedron, 1996, 27, 9161.
- [30] J.N. Low, J. Cobo, C. Garcia, M. Melguizo, M. Nogueras, A. Sanchez, C. Gildewell, Acta Crystallogr. Sect. C, 2001, C57, 597.
- [31] Y .S. Kayukov, I.N. Bardasov, O.V. Kayukova, O.V. Ershov, O.E. Nasakin, J. Org. Chem., 2010, 46, 1266.
- [32] M . Hapke, K. Kral, Ch. Fischer, A. Spannenberg, A. Gutnov, D. Redkin, B. Heller, J. Org. Chem., 2010, 75, 3993.
- [33] V .S. Barseneva, V.A. Bakulev, W. Dehaen, S. Toppet, M. Borovkova, Tetrahedron, 2007, 63, 4491.
- [34] M .R. Shaaban, R. El-Sayed, A.H.M. Elwahy, Tetrahedron, 2011, 67, 6111.
- [35] H . Śladowska, D. Szkatuła, B. Filipek, D. Maciąg, J. Sapa, M. Zygmunt, Pharmazie, 2001, 56, 133.
- [36] H . Śladowska, B. Filipek, D. Szkatuła, A. Sabiniarz, M. Kardasz, J. Potoczek, M. Sieklucka-Dziuba, G. Rajtar, Z. Kleinrok, T. Lis, Il Farmaco, 2002, 57, 897.
- [37] H . Śladowska, B. Filipek, D. Szkatuła, J. Sapa, M. Bednarski, M. Ciołkowska, Il Farmaco, 2005, 60, 53.
- [38] H . Śladowska, A. Sabiniarz, D. Szkatuła, B. Filipek, J. Sapa, Acta Pol. Pharm., 2006, 63, 245.
- [39] F . Da Settimo, A.M. Marini, C. La Motta, F. Simorini, E. Luchetti, S. Bertini, Farmaco, 1996, 51, 725.
- [40] X. Wu, PCT Int. Appl., 2002, WO 20020613 A1 20020613.
- [41] P.K. Pooni, K.J. Merchant, C.M. Kerr, D. Harrison, PCT Int. Appl., 2011, WO 2011083316 A1 20110714.
- [42] A .M. Chollet, T. Le Diguarher, N. Kucharczyk, A. Loynel, M. Bertrand, G. Trucker, N. Guilbaund, M. Burbridge, P. Pastoureau, A. Fradin, M. Sabatini, J-L. Fauchere, P. Casara, Bioorg. Med. Chem., 2002, 10, 531.
- [43] C . Deraeve, I.M. Dorobantu, F. Rebbah, F. Le Quemener, P. Constant, A. Quemard, V. Bernardes-Genisson, J. Bernardou, G. Pratviel, Bioorg. Med. Chem., 2011, 19, 6225.
- [44] L .J.S. Knutsen, A.G. Lundemose, C.B. Jeppesen, A.R. Sorensen, G.M. Danielsen, PCT Int. Appl., 1999, WO , 9931098 A1 19990624.
- [45] G .W. Muller, PCT Int. Appl., 1995, WO 9501348 A2 19950112.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-91dea2ba-7f0a-4552-b85f-d84d4789c055
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.