Synteza i aktywność biologiczna pochodnych 2,6-naftyrydyny

• Autorzy: Wójcicka A. , Wagner E.

Warianty tytułu

EN

Synthesis and biological activity of 2,6-nap hthyridine derivatives

• Języki publikacji: PL

Abstrakty

EN

2,6-Naphthyridine is one of the six structural isomers of pyridopyridines. This review presents most of the literature data about natural and synthetic 2,6-naphthyridine derivatives and their biological activity. The main goal of this paper is to present various methods for the preparation of 2,6-naphthyridine analogues. Compounds containing 2,6-naphthyridine moiety can be synthesized from different substrates. Most of them have been obtained by cyclocondensation of various pyridine derivatives. During the past twenty years the biological activity of 2,6-naphthyridines have been studied. Presented compounds exhibit anticancer [21, 41], antihypertension [10], and antidepression [25] activity. Some of them can be used in the treatment of heart diseases [22], appetite disturbance, and obsessive states [43, 44]. 2,6-Naphthyridine derivatives with different molecular targets, e.g. topoisomerase [41], SERT [27], and protein kinases [21, 22] inhibitors have also been reported. Many of the 2,6-naphthyridine analogues are histamine H3 [27] and serotonine 5-HT2 [42–44] receptor antagonists.

Słowa kluczowe

PL

pochodne 2,6-naftyrydyny; synteza; aktywność biologiczna

EN

2,6-naphthyridine derivatives; synthesis; biological activity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2012
• Tom: [Z] 66, 3-4
• Strony: 297--318
• Opis fizyczny: Bibliogr. 48 poz., schem.

Twórcy

autor

Wójcicka A.

autor

Wagner E.

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

Bibliografia

• [1] G .Y. Lesher, E.J. Froelich, M.D. Gruett, J.H. Bailery, R.P. Brundage, J. Med. Pharm. Chem., 1962, 91, 1063.
• [2] A . Wójcicka, E. Wagner, Wiad. Chem., 2011, 65, 235.
• [3] S . Gabriel, J. Colman, Chem. Ber., 1902, 35, 1358.
• [4] G . Barger, J. Madaniveitia, P. Streuli, J. Chem. Soc., 1939, 510.
• [5] W. Carruthers, Some modern methods of organic synthesis, Syndics of the Cambridge Univerity Press, 1971, 65.
• [6] R .H. Menske, H.L. Holmes, R.G. Rodrigo, The Alkaloids. Chemistry and Physiology, 1971, 7, 149.
• [7] T . Kobayashi, R. Kikumoto, Tetrahedron, 1962, 18, 813.
• [8] K.J. Harkiss, D. Swift, Tetrahedron Lett., 1970, 55, 4773.
• [9] K.J. Harkiss, Phytochemistry, 1971, 10, 2849.
• [10] G er. Pat. 3 336 194, Ref. Zh. Khim., 1986, 10 (O) 13P.
• [11] A . Taurins, R. Tan, Can. J. Chem., 1974, 52, 843.
• [12] R . Tan, A. Taurins, Tetrahedron Lett., 1965, 31, 2737.
• [13] U .N. Rao, X. Han, E.R. Biehl, Arkivoc, 2002, 10, 61.
• [14] X. Han, E.R. Biehl, Arkivoc, 2002, 10, 40.
• [15] F . Alhaique, F.M. Riccieri, E. Santucci, Tetrahedron Lett., 1975, 3, 173.
• [16] H.J.W. van den Haak, H.C. van der Plas, B. van Veldhuizen, J. Heterocyclic Chem., 1981, 18, 1349.
• [17] F . Alhaique, F.M. Riccieri, E. Santucci, Il Farmaco, 1983, 38, 242.
• [18] D .E. Ames, W.W. Dodds, J. Chem. Soc. Perkin I, 1972, 5, 705.
• [19] F . Alhaique, F.M. Riccieri, E. Santucci, Gazz. Chim. Ital., 1975, 105, 1001.
• [20] G . Giacomello, F. Gualtieri, F.M. Riccieri, M.L. Stein, Tetrahedron Lett., 1965, 16, 1117.
• [21] F . Pierre, P.C. Chua, S.E. O'Brien, A. Siddiqui-Jain, P. Bourbon, M. Haddach, J. Michaux, J. Nagasawa, M.K. Schwaebe, E. Stefan, A. Vialettes, J.P. Whitten, T.K. Chen, L. Darjania, R. Stansfield, K. A nderes, J. Bliesath, D. Drygin, C. Ho, M. Omori, C. Proffitt, N. Streiner, K. Trent, W.G. Rice, D.M. Ryckman, J. Med. Chem., 2011, 54, 635.
• [22] E .L. Meredith, O. Ardayfio, K. Beattie, M.R. Dobler, I. Enyedy, C. Gaul, V. Hosagrahara, C. Jewell, K. Koch, W. Lee, H.J. Lehmann, T.A. McKinsey, K. Miranda, N. Pagratis, M. Pancost, A. Patnaik, D. Phan, C. Plato, M. Qian, V. Rajaraman, C. Rao, O. Rozhitskaya, T. Ruppen, J. Shi, S. J. Siska, C. S pringer, M van Eis, R.B. Vega, A von Matt, L. Yang, T. Yoon, J. Zhang, N. Zhu, L.G. Monovich, J. Med. Chem., 2010, 53, 5400.
• [23] Y . Ikeura, T. Tanaka, Y. Kiyota, S. Morimoto, M. Ogino, T. Ishimaru, I. Kamo, T. Doi, H. Natsugari, Chem. Pharm. Bull., 1997, 45, 1642.
• [24] T . Sakamoto, Y. Kondo, H. Yamanaka, Chem. Pharm. Bull., 1985, 33, 626.
• [25] E .M. Stocking, M.A. Letavic, P. Bonaventure, N.I. Carruthers, Curr. Top. Med. Chem., 2010, 5, 596.
• [26] P . Molin, A. Lorenzo, E. Aller, Tetrahedron, 1992, 48, 4601.
• [27] M.A. Letavic, J.M. Keith, K.S. Ly, A.J. Barbier, J.D. Boggs, S.J. Wilson, B. Lord, T.W. Lovenberg, N.I. Carruthers, Bioorg. Med. Chem. Lett., 2007, 17, 2566.
• [28] T .L. Fisher, D.E. Metzler, J. Am. Chem. Soc., 1969, 10, 5323.
• [29] A . Numata, Y. Kondo, T. Sakamoto, Synthesis, 1999, 2, 306.
• [30] C .K. Govindan, G. Taylor, J. Org. Chem., 1983, 48, 5348.
• [31] L.E. Brieaddy, S.W. Mascarella, H.A. Navarro, R.N. Atkinson, M.I. Damaj, B.R. Martin, F.I. Carroll, Tetrahedron Lett., 2001, 42, 3795.
• [32] S . Mataka, K. Takahashi, M. Tashiro, J. Heterocyclic Chem., 1983, 20, 971.
• [33] J .E. Macor, W. Kuipers, R.J. Lachicotte, Chem. Commun., 1998, 9, 983.
• [34] D . Baranowska, Molecules, 2005, 10, 265.
• [35] I.A. Perillo, L.D. Kremenchuzky, M.M. Blanco, J. Mol. Structure, 2009, 921, 307.
• [36] M. Nasr, H.H. Zoorb, A. Zayed, M.T. El-Wassimi, Monatsh. Chem., 1979, 110, 913.
• [37] A . Chilin, P. Manzini, A. Confente, G. Pastorini, A. Guiotto, Tetrahedron, 2002, 58, 9959.
• [38] H. Irikawa, N. Adachi, H. Muraoka, Heterocycles, 1998, 48, 1415.
• [39] F . Tjosas, N.M. Pettersen, A. Fiksdahl, Tetrahedron, 2007, 63, 11893.
• [40] A .l. Ruchelman, S. Zhu, N. Zhou, A. Liu, L. F. Liu, E.J. LaVoie, Bioorg. Med. Chem. Lett., 2004, 14, 5585.
• [41] S . Zhu, A.l. Ruchelman, N. Zhou, A. Liu, L.F. Liu, E.J. LaVoie, Bioorg. Med. Chem. Lett., 2006, 16, 3131.
• [42] J . Nozulak, H.O. Kalkman, P. Floersheim, D. Hoyer, P. Schoeffter, H.R. Buerki, J. Med. Chem., 1995, 38, 28.
• [43] BRD P. 473 550, Chem. Abstr., 1992, 117, 111 583.
• [44] BRD P. 4 027 018, Ref. Zh. Khim., 1993, 2 O 76P.
• [45] V. Gracias, K.E. Frank, G.L. Milligan, J. Aube, Tetrahedron, 1997, 53, 16241.
• [46] J . Ritter, R. Gleiter, Liebigs Ann. Chem./Recl., 1997, 1179.
• [47] G . Haberhauer, R. Gleiter, J. Am. Chem. Soc., 1999, 121, 4664.
• [48] N .S. Ibrahim, K.U. Sadek, S.I. Aziz, M.H. Elnagdi, Z. Naturforsch. B, 1985, 40b, 129.