Identyfikatory
Warianty tytułu
Synthesis of pyrazolo[4,3-c]heterocyclic derivatives
Języki publikacji
Abstrakty
The broad spectrum of biological activity of pyrazolo[4,3-c]heterocyclic derivatives is the main of reason for the preparation of new compounds containing this scaffold. This review presents most of the literature data on the synthesis of pyrazolo[ 4,3-c]heterocyclic derivatives. This isomer system containing pyrazole moiety condensed with a heterocyclic ring can be synthesized from a different substrates, but that synthesis may be classified into two main categories: annulation of the pyrazole ring onto heterocyclic derivatives or annulation of the heterocyclic ring onto pyrazole analogs. The main goal of this study is the presentation of various methods for the preparation of the pyrazolo[4,3-c]pyridine (Rys. 2) [1–15], pyrazolo[4,3-c] quinoline (Rys. 3) [16–63], pyrazolo[4,3-c]isoquinoline [64, 65], pyrazolo[4,3-c] naphthtyridine [66–68], pyrazolo[4,3-c]thiazine [69–72], pyrazolo[4,3-c]cinnoline [73, 74], pyrazolo[4,3-c]quinolizine [75], and pyrazolo[4,3-c]pyridazine [76] derivatives.
Wydawca
Czasopismo
Rocznik
Tom
Strony
1075--1104
Opis fizyczny
Bibliogr. 76 poz., schem.
Twórcy
autor
- Katedra i Zakład Technologii Leków, Uniwersytet Medyczny im. Piastów Śląskich we Wrocławiu ul. Borowska 211A, 50-556 Wrocław
Bibliografia
- [1] R.A. Mekheimer, E.A. Ahmed, K.U. Sadek, Tetrahedron, 2012, 68, 1637.
- [2] L.A. Zhmurenko, G.M. Molodavkin, T.A. Voronina, V.P. Lezina, J. Pharm. Chem., 2012, 46, 18.
- [3] C.D. Benham, T.P. Blackburn, A. Johns, N.R. Kotecha, R.T. Martin, D.R. Thomas, M. Thompson, R.W. Ward, Bioorg. Med. Chem. Lett., 1995, 5, 2455.
- [4] D. Zerovnik, U. Groselj, D. Kralj, C. Malavasic, J. Bezensek, G. Dahmann, K. Stare, A. Meden, B. Stanovnik, J. Svete, Synthesis, 2010, 19, 3363.
- [5] M.A. Al-Omar, K.M. Youssef, M.A. El-Sherbeny, A.A. Awadalla, H.I. El-Subbagh, Arch. Pharm. Chem. Life Sci., 2005, 338, 175.
- [6] S.A.F. Rostom, G.S. Hassan, H.I. El-Subbagh, Arch. Pharm. Chem. Life Sci., 2009, 342, 584.
- [7] S. Rostamizdeh, N. Shadjou, M. Azad, N. Jalali, Catal. Comm., 2012, 26, 218.
- [8] P. Yogeeswari, M. Sharma, G. Samala, M. Gangadhar, S. Karthick, S. Mallipeddi, A. Semwal, D. Sriram, Eur. J. Med. Chem., 2013, 66, 211.
- [9] W.P. Blackaby, J.R. Atack, F. Bromidge, R. Lewis, M.G.N. Russell, A. Smith, K. Wafford, R.M. McKernan, L.J. Street, J.L. Castro, Bioorg. Med. Chem. Lett., 2005, 15, 4998.
- [10] A.W. Garofalo, J.J. Jagodzinski, A.W. Konradi, R.A. Ng, C.M. Semko, H.L. Sham, M. Sun, X.M. Ye, Chem. Pharm. Bull., 2012, 60, 1063.
- [11] W.J. Lominac, M.L. D’Angelo, M.D. Smith, D.A. Ollison, J.M. Hanna Jr., Tetrahedron Lett., 2012, 53, 906.
- [12] N. Laugiakis, P. Marakos, N. Poul, J. Balzarini, Chem. Pharm. Bull., 2008, 56, 775.
- [13] H.M. Faidallah, S.A.F. Rostom, M.S. Al-Saadi, JKAU: Sci., 2010, 22, 177.
- [14] S. Kushwah, K. Prajapati, N. Darji, P. Soni, P. Shah, IJPRBS, 2012, 1, 287.
- [15] J. Baskovc, D. Bevk, B. Stanovnik, J. Steve, J. Comb. Chem., 2009, 11, 500.
- [16] R.I. Fryer, P. Zhang, R. Rios, Z. Gu, A.S. Basile, P. Skolnick, J. Med. Chem., 1993, 36, 1669.
- [17] L. Savini, L. Chiasserini, C. Pellerano, G. Biggio, E. Maciocco, M. Serra, N. Cinone, A. Carrieri, C. Altomare, A. Carotti, Bioorg. Med. Chem. Lett., 2001, 9, 431.
- [18] L. Savini, P. Massarelli, C. Nencini, C. Pellerano, G. Biggio, A. Maciocco, G. Tuligi, A. Carrieri, N. Cinone, A. Carotti, Bioorg. Med. Chem. Lett., 1998, 6, 389.
- [19] A. Carotti, C. Altomare, L. Savini, L. Chiasserini, C. Pellerano, M.P. Mascia, E. Maciocco, F. Busonero, M. Mameli, G. Biggio, E. Sanna, Bioorg. Med. Chem. Lett., 2003, 11, 5259.
- [20] N. Yokoyama, B. Ritter, A.D. Neubert, J. Med. Chem., 1982, 25, 337.
- [21] L. Ismaili, B. Refouvelet, F.J. Robert, J. Heterocycl. Chem., 1999, 36, 719.
- [22] B.K. Ghotekar, M.G. Ghagare, R.B. Toche, M.N. Jachak, Monatsh. Chem., 2010, 141, 169.
- [23] J. Karolak-Wojciechowska, J. Lange, W. Ksiazek, M. Gniewosz, S. Rump, Farmaco, 1993, 48, 65.
- [24] C. Manera, M.G. Cascio, V. Benetti, M. Allara, T. Tuccinardi, A. Martinelli, G. Saccomanni, E. Vivoli, C. Ghelardini, V.D. Marzo, P.L. Ferrarini, Bioorg. Med. Chem. Lett., 2007, 17, 6505.
- [25] R.M.J. Lopez, E. L. Moyano, G.I. Yranzo, Tetrahedron Lett., 2010, 51, 478.
- [26] R.R. Reis, E.C. Azevedo, M.C.B.V. de Souza, V.F. Ferreira, R.C. Montenegro, A.J. Araujo, C. Pessoa, L.V. Costa-Lotufo, M.O. de Moraes, J.D.B.M. Filho, A.M.T. de Souza, N.C. de Carvalho, H.C. Castro, C.R. Rodrigues, T.R.A. Vasconcelos, Eur. J. Med. Chem., 2011, 46, 1448.
- [27] H. Budgaard, N.M. Nielsen, J. Med. Chem., 1987, 30, 454.
- [28] S. Takada, H. Shindo, T. Sasatani, N. Chomei, A. Matsushita, J. Med. Chem., 1989, 32, 1213.
- [29] I.M. Crespo, J. Gracia, C. Puig, A. Vega, J. Bou, J. Beleta, T. Domenech, H. Ryder, V. Segarra, J.M. Palacios, Bioorg. Med. Chem. Lett., 2000, 10, 2661.
- [30] B. Baruah, K. Dasu, B. Vaitilingam, A. Vanguri, S.R. Casturi, K.R. Yeleswarapu, Bioorg. Med. Chem. Lett., 2004, 14, 445.
- [31] I.V. Ukrainets, A.A. Tkach, V.V. Kravtsova, A.V. Turov, Chem. Heterocycl. Comp., 2009, 45, 48.
- [32] S. Chimichi, M. Boccalini, A. Matteucci, Tetrahedron, 2008, 64, 9275.
- [33] Th. Kappe, W. Stadlbauer, Molecules, 1996, 1, 255.
- [34] W. Stadlbauer, G. Hojas, J. Heterocyclic Chem., 2004, 41, 681.
- [35] M. Abass, Synth. Commun., 2000, 30, 2735.
- [36] F. Suzuki, Y. Nakasato, K. Ohmori, T. Tamura, H. Hosoe, K. Kubo, I. Yoshitake, Eur. Patent 476544, 1992.
- [37] R. Mekheimer, E.Kh. Ahmed, A.F. Khattab, Bull. Chem. Soc. Jpn., 1993, 66, 2936.
- [38] A.R Mekheimer, S.M. Refaey, K.U. Sadek, A.M. Abdel Hameed, M.A. Ibrahim, A. Shah, J. Chem. Res., 2008, 735.
- [39] A.R Mekheimer, E.Kh. Ahmed, H.A. El-Faham, L.H. Kamel, D. Doepp, J. Chem. Res., 2003, 288.
- [40] R. Mekheimer, Pharmazie, 1994, 49, 486.
- [41] R. Mekheimer, T. Kappe, Heterocycl. Commun., 1998, 4, 131.
- [42] M.X. Wang, Y. Liu, Z.T. Huang, Tetrahedron Lett., 2001, 42, 2553.
- [43] O.V. Silin, T.I. Savchenko, S.M. Kovalenko, V.M. Nikitchenko, A.V. Ivachtchenko, Heterocycles, 2004, 63, 1883.
- [44] T.I. Savchenko, O.V. Silin, S.M. Kovalenko, V.I. Musatov, V.M. Nikitchenko, A.V. Ivachtchenko, Synth. Commun., 2007, 37, 1321.
- [45] G.D. Kalayanov, S.K. Kang, H.G. Cheon, S.G. Lee,E.K. Yum, S.S. Kim, J.K. Choi, Bull. Korean, Chem. Soc., 1998, 19, 667.
- [46] K.N. Sangwan, M.P. Kelkar, N.S. Rastogi, N. Anand, Indian J. Chem. Sect B: Org. Chem. Incl. Med. Chem., 1985, 24B, 639.
- [47] G.D. Kalayanov, J.K. Choi, Heterocycles, 1998, 48, 1221.
- [48] J. Pawlas, P. Vedso, P. Jacobsen, P.O. Huusfeldt, M. Begtrup, J. Org. Chem., 2000, 65, 9001.
- [49] D. Sicker, D. Reifegerste, S. Hauptmann, H. Wilde, G. Mann, Synthesis, 1985, 3, 331.
- [50] F. Melani, L. Cecchi, G. Palazzino, G. Filacchioni, C. Martini, E. Pennacchi, A. Lucacchini, J. Pharm. Sci., 1986, 75, 1175.
- [51] K. Makino, H.S. Kim, Y. Kurosawa, J. Heterocycl. Chem., 1998, 35, 489.
- [52] P.G. Baraldi, M.A. Tabrizi, D. Preti, A. Bovero, F. Fruttarolo, R. Romagnoli, N.A. Zaid, A.R. Moorman, K. Varani, P.A. Borea, J. Med. Chem., 2005, 48, 5001.
- [53] B. Daou, M. Soufiaoui, Tetrahedron, 1989, 45, 3351.
- [54] J. Pawlas, P. Vedso, P. Jacobsen, P.O. Huusfeldt, M. Begtrup, J. Org. Chem., 2001, 66, 4214.
- [55] A.P. Truong, D.L. Aubele, G.D. Probst, M.I. Neitzel, C.M. Semko, S. Bowers, D. Dressen, R.K. Hom, A.W. Konradi, H.L. Sham, A.W. Garofalo, P.S. Keim, J. Wu, M.S. Dappen, K. Wong, E. Goldbach, K.P. Quinn, J.M. Sauer, E.F. Brigham, W. Wallace, L. Nguyen, S.S. Hemphill, M.P. Bova, G. Basi, Bioorg. Med. Chem. Lett., 2009, 19, 4920.
- [56] D.C. Beshore, R. M. Dipardo, S.D. Kuduk, Tetrahedron Lett., 2010, 51, 970.
- [57] M.S. Christodoulou, S. Liekens, K.M. Kasiotis, S.A. Haroutounian, Bioorg. Med. Chem., 2010, 18, 4338.
- [58] S. Duggineni, D. Sawant, B. Saha, B. Kundu, Tetrahedron, 2006, 62, 3228.
- [59] G.T. Cin, S. Demirel, A. Cakici, J. Organomet. Chem., 2011, 696, 613.
- [60] M. Gal, O. Feher, E. Tihanyi, G. Horvath, G. Jerkovich, G. Argay, A. Kalman, Tetrahedron Lett., 1980, 21, 1567.
- [61] M. Gal, O. Feher, E. Tihanyi, G. Horvath, G. Jerkovich, Tetrahedron 1982, 38, 2933.
- [62] K.S. Phadtare, K.S. Kamat, T.G. Panse, Indian J. Chem., 1983, 22B, 499.
- [63] M.G. Ferlin, G. Chiarelotto, S. Dall’Acqua, E. Maciocco, M.P. Mascia, M.G. Pisu, G. Biggio, Bioorg. Med. Chem, 2005, 13, 3531.
- [64] E.D. Philips, S.C. Hirst, M.W.D. Perry, J. Withnall, J. Org. Chem., 2003, 68, 8700.
- [65] J. Mortier, R. Frederick, C. Ganeff, C. Remouchamps, P. Talaga, L. Pochet, J. Wouters, J. Piette, E. Dejardin, B. Masereel, Bioch. Pharm., 2010, 79, 1462.
- [66] A. Da Settimo, G. Primafiore, F. Da Settimo, F. Simorini, Drug Des. Disc., 1994, 11, 307.
- [67] I.T. Forbes, C.N. Johnson, G.E. Jones, J. Loudon, J.M. Nicholass, M. Thompson, N. Upton, J. Med. Chem., 1990, 33, 2640.
- [68] W. Fan, Q. Ye, H-W. Xu, B. Jiang, S-L. Wang, S-J. Tu, Org. Lett., 2013, 15, 2258.
- [69] W. Malinka, Il Farmaco, 1995, 50, 29.
- [70] S. Sabatini, F. Gosetto, S. Serritella, G. Manfroni, O. Tabarrini, N. Iraci, J.P. Brincat, E. Carosati, M. Villarini, G.W. Kaatz, V. Cecchetti, J. Med. Chem., 2012, 55, 3568.
- [71] N. Tomita, Y. Hayashi, S. Suzuki, Y. Oomori, Y. Aramaki, Y. Matsushita, M. Iwatani, H. Iwata, A. Okabe, Y. Awazu, O. Isono, R.J. Skene, D.J. Hosfield, H. Miki, T. Kawamoto, A. Hori, A. Baba, Bioorg. Med. Chem. Lett., 2013, 23, 1779.
- [72] O. Migliara, V. Spano, B. Parrino, C. Ciancimino, P. Diana, Arkivoc, 2012, ii, 41.
- [73] A.M. Amer, I.A.G. Attia, M. El-Mobayad, S. Asker, Polish J. Chem., 2000, 74, 681.
- [74] R.K. Tonk, S. Bawa, G. Chawla, G.S. Deora, S. Kumar, V. Rathore, N. Mulakayala, A. Rajaram, A.M. Kalle, O. Afzal, Eur. J. Med. Chem., 2012, 57, 176.
- [75] V.A. Chebanov, V.E. Saraev, S.M. Desenko,V.N. Chernenko, I.V. Knyazeva, U. Groth, T.N. Glasnov, C.O Kappe, J. Org. Chem., 2008, 73, 5110.
- [76] L. Filak, T.A. Rokob, G. A. Vasko, O. Egyed, A. Gomory, Z. Riedl, G. Hajos, J. Org. Chem., 2008, 73, 3900.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-5b0ecc51-9a50-4ca4-a1bd-f2f95e984591