Abstract
The review compiles the strategies and methods of development of aminopyrimidine derivatives as targeted antitumor pharmaceuticals. The advances in organic and heterocyclic chemistry are considered in the targeted synthesis of aminopyrimidine derivatives whose series contains the most demanded and efficient antitrumor pharmaceuticals. The problems of preparation of compounds with multikinase activity profile and the construction of chimeric molecules are discussed.
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Newman, D.J. and Cragg, G.M., J. Nat. Prod., 2007, vol. 70, p. 461.
Bade, R., Chan, Ho-F., and Reynisson, J., Eur. J. Med. Chem., 2010, vol. 45, p. 5646.
Imyanitov, E.N., Prakt. Onkol., 2010, vol. 11, p. 123.
Kuban’i, G., Ros. Khim. Zh., 2006, vol. 50, p. 5.
Ghose, A.K., Herbertz, T., Pippin, D.A., Salvino, J.M., and Mallamo, J.P., J. Med. Chem., 2008, vol. 51, p. 5149.
Gozalbes, R., Simon, L., Froloff, N., Sartori, E., Monteils, C., and Baudelle, R., J. Med. Chem., 2008, vol. 51, p. 3124.
Marzaro, G., Chilin, A., Guiotto, A., Uriarte, E., Brun, P., Castagliuolo, I., Tonus, F., and González-Díaz, H., Eur. J. Med. Chem., 2011, vol. 46, p. 2185.
Sun, X., Chen, L., Li, Y., Li, W., Liu, G., Tu, Y., and Tang, Y., Acta Pharm. Sin., 2014, vol. 35, p. 301.
Paez, J.G., Jänne, P.A., Lee, J.C., Tracy, S., Greulich, H., Gabriel, S., Herman, P., Kaye, F.J., Lindeman, N., Boggon, T.J., Naoki, K., Sasaki, H., Fujii, Y., Eck, M.J., Sellers, W.R., Johnson, B.E., and Meyerson, M., Science, 2004, vol. 304, p. 1497.
Druker, B.J., Talpaz, M., Resta, D.J., Peng, B., Buchdunger, E., Ford, J.M., Lydon, N.B., Kantarjian, H., Capdeville, R., Ohno-Jones, S., and Sawyers, C.L., N. Engl. J. Med., 2001, vol. 344, p. 1031.
Liao, J.J., J. Med. Chem., 2007, vol. 50, p. 409.
Zimmermann, J., Buchdunger, E., Mett, H., Meyer, T., and Lydon, N.B., Bioorg. Med. Chem. Lett., 1997, vol. 7, p. 187.
Druker, B.J., Tamura, S., Buchdunger, E., Ohno, S., Segal, G.M., Fanning, S., Zimmermann, J., and Lydon, N.B., Nat. Med., 1996, vol. 2, p. 561.
Barker, A.J., Gibson, K.H., Grundy, W., Godfrey, A.A., Barlow, J.J., Healy, M.P., Woodburn, J.R., Ashton, S.E., Curry, B.J., Scarlett, L., Henthorn, L., and Richards, L., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1911.
Moyer, J.D., Barbacci, E.G., Iwata, K.K., Arnold, L., Boman, B., Cunningham, A., di Orio, C., Doty, J., Morin, M.J., Moyer, M.P., Neveu, M., Pollack, V.A., Pustilnik, L.R., Reynolds, M.M., Sloan, D., Theleman, A., and Miller, P., Cancer Res., 1997, vol. 57, p. 4838.
Lowinger, T.B., Riedl, B., Dumas, J., and Smith, R.A., Curr. Pharm. Des., 2002, vol. 8, p. 2269.
Sun, L., Liang, C., Shirazian, S., Zhou, Y., Miller, T., Cui, J., Fukuda, J.Y., Chu, J.Y., Nematalla, A., Wang, X., Chen, H., Sistla, A., Luu, T.C., Tang, F., Wei, J., and Tang, C., J. Med. Chem., 2003, vol. 46, p. 1116.
Lombardo, L.J., Lee, F.Y., Chen, P., Norris, D., Barrish, J.C., Behnia, K., Castaneda, S., Cornelius, L.A., Das, J., Doweyko, A.M., Fairchild, C., Hunt, J.T., Inigo, I., Johnston, K., Kamath, A., Kan, D., Klei, H., Marathe, P., Pang, S., Peterson, R., Pitt, S., Schieven, G.L., Schmidt, R.J., Tokarski, J., Wen, M.L., Wityak, J., and Borzilleri, R.M., J. Med. Chem., 2004, vol. 47, p. 6658.
LaRusso, P.M. and Eder, J.P., Expert Opin. Invesigt. Drugs, 2008, vol. 17, p. 1013.
Drygin, D., Haddach, M., Pierre, F., and Ryckman, D.M., J. Med. Chem., 2012, vol. 55, p. 8199.
Zhan, W., Li, D., Che, J., Zhang, L., Yang, B., Hu, Y., Liu, T., and Dong, X., Eur. J. Med. Chem., 2014, vol. 75, p. 11.
Golovko, Yu.S., Ivashkevich, O.A., and Golovko, A.S., Vestn. BGU, Ser. 2, Khim. Biol. Geogr., 2012, p. 7.
Thomsen, R. and Christensen, M.H., J. Med. Chem., 2006, vol. 49, p. 3315.
Liao, J.J., J. Med. Chem., 2007, vol. 50, p. 409.
Knighton, D.R., Zheng, J.H., Ten Eyck, L.F., Ashford, V.A., Xuong, N.H., Taylor, S.S., and Sowadski, J.M., Science, 1991, vol. 253, p. 407.
Cheek, S., Ginalski, K., Zhang, H., and Grishin, N.V., BMC Struct. Biol., 2005, vol. 5, p. 1.
Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Adv. Drug Deliv. Rev., 1997, vol. 23, p. 3.
Lipinski, C.A., Drug Discovery Today Technol., 2004, vol. 1, p. 337.
Kaserer, T., Temml, V., Kutil, Z., Vanek, T., Landa, P., and Schuster, D., Eur. J. Med. Chem., 2015, vol. 96, p. 445.
Witek, J., Smusz, S., Rataj, K., Mordalski, S., and Bojarski, A.J., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 580.
Shen, Q., Chemometr. Intell. Lab. Syst., 2006, vol. 82, p. 44.
Leung, Ch.S., Leung, S.F., Tirado-Rives, J., and Jorgensen, W.L., J. Med. Chem., 2012, vol. 55, p. 4489.
Golovko, Yu.S., Ivashkevich, O.A., Matulis, V.E., and Gaponik, P.N., Khimicheskie problemy sozdaniya novykh materialov i tekhnologii, Ivashkevich, O.A., Ed., Minsk: Izd. BGU, 2008, vol. 3.
Höltje, H.-D., Sippl, W., Rognan, D., and Folkers, G., Molecular Modeling. Basic Principles and Applications, Weinheim: Wiley–VCH, 2008, 3rd ed.
Filimonov, D.A. and Poroikov, V.V., Ros. Khim. Zh., 2006, vol. 50, p. 66.
Silverman, R.B., The Organic Chemistry of Drug Design and Drug Action, San Diego: Elsevier Academic Press, 2004.
Young, D.C., Computational Drug Design. A Guide for Computational and Medicinal Chemists, Hoboken: John Wiley & Sons Inc., 2001.
Cherkasov, A., Muratov, E.N., Fourches, D., Varnek, A., Baskin, I.I., Cronin, M., Dearden, J., Gramatica, P., Martin, Y.C., Todeschini, R., Consonni, V., Kuz’min, V.E., Cramer, R., Benigni, R., Yang, Ch., Rathman, J., Terfloth, L., Gasteiger, J., Richard, A., and Tropsha, A., J. Med. Chem., 2014, vol. 57, p. 4977.
Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Fundamentals of Organic Chemistry of Medicines), Moscow: BINOM. Laboratoriya znanii, 2007.
Poroikov, V.V., Filimonov, D.A., Borodina, Yu.V., Lagunin, A.A., and Kos, A., J. Chem. Inform. Comput. Sci., 2000, vol. 40, p. 1351.
Anzali, S., Barnickel, G., Cezanne, B., Krug, M., Filimonov, D., and Poroikov, V., J. Med. Chem., 2001, vol. 4, p. 2432.
Koroleva, E.V., Gusak, K.N., and Ignatovich, Zh.V., Russ. Chem. Rev., 2010, vol. 79, p. 655.
Kankan, R.N. and Rao, D.R., WO Patent no. 074502, 2004; Chem. Abstr., 2004, vol. 141, no. 207230.
Huang, W.-Sh. and Shakespeare, W.C., Synthesis, 2007, p. 2121.
Chu, X.-J., Depinto, W., Bartkovitz, D., So, S.-S., Vu, B.T., Packman, K., Lukacs, C., Ding, Q., Jiang, N., Wang, K., Goelzer, P., Yin, X., Smith, M.A., Higgins, B.X., Chen, Y., Xiang, Q., Moliterni, J., Kaplan, G., Graves, B., Lovey, A., and Fotouhi, N., J. Med. Chem., 2006, vol. 49, p. 6549.
Echalierb, A., Bettayeb, K., Ferandin, Y., Lozach, O., Clément, M., Valette, A., Liger, F., Marquet, B., Morris, J.C., Endicott, J.A., Joseph, B., and Meijer, L., J. Med. Chem., 2008, vol. 51, p. 737.
Qi, H., Chen, L., Liu, B., Wang, X., Long, L., and Liu, D., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 1108.
Cui, J., Fu, R., Zhou, L.-H., Chen, Sh.-P., Lia, G.-W., Qian, Sh.-X., and Liu, Sh., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2442.
Lü, Sh., Luo, Q., Hao, X., Li, X., Ji, L., Zheng, W., and Wang, F., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 6964.
Schenone, S., Brullo, C., and Botta, M., Curr. Med. Chem., 2010, vol. 17, p. 1220.
Radi, M., Tintori, C., Cusumeci, F., Brullo, C., Zampetini, C., Dreassi, E., Falacara, A.L., Vignaroli, G., Crespan, E., Zanoli, S., Laurenzana, I., Filippi, I., Maga, G., Schenone, S., Angelucci, A., and Botta, M., J. Med. Chem., 2013, vol. 56, p. 5382.
Duveau, D.Y., Hu, X., Walsh, M.J., Shukl, S., Skoumbourdis, A.P., Boxer, M.B., Ambudkar, S.V., Shen, M., and Thomas, C.J., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 682.
Chai, B., Wanga, Sh., Yu, W., Li, H., Song, Ch., Xu, Y., Liu, Ch., and Chang, J., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 3505.
Zhou, W., Ercan, D., Jänne, P.A., and Gray, N.S., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 638.
Han, Ch., Wan, L., Ji, H., Ding, K., Huang, Zh., Lai, Y., Peng, S., and Zhang, Y., Eur. J. Med. Chem., 2014, vol. 77, p. 75.
Park, C.H., Choe, H., Jang, I.-Y., Kwon, S.Y., Latif, M., Lee, H.K., Lee, H.J., Yang, E.H., Yun, J.I., Chae, Ch.H., Cho, S.Y., Choi, S.U., Ha, J.D., Jung, H., Kim, H.R., Kim, P., Lee, C.O., Yun, Ch.S., and Lee, K., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6192.
Zificsak, C.A., Theroff, J.P., Aimone, L.D., Angeles, T.S., Albom, M.S., Cheng, M., Mesaros, E.F., Ott, G.R., Quail, M.R., Underiner, T.L., Wan, W., and Dorsey, B.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 3877.
Mesaros, E.F., Burke, J.P., Parrish, J.D., Dugan, B.J., Anzalone, A.V., Angeles, T.S., Albom, M.S., Aimone, L.D., Quail, M.R., Wan, W., Lu, L., Huang, Z., Ator, M.A., Ruggeri, B.A., Cheng, M., Ott, G.R., and Dorsey, B.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 463.
Reuman, M., Beish, S., Davis, J., Batchelor, M.J., Hutchings, M.C., Moffat, D.F.C., Connolly, P.J., and Russell, R.K., J. Org. Chem., 2008, vol. 73, p. 1121.
Martin, M.W., Newcomb, J., Nunes, J.J., McGowan, D.C., Armistead, D.M, Boucher, C., Buchanan, J.L., Buckner, W., Chai, L., Elbaum, D., Epstein, L.F., Faust, T., Flynn, S., Gallant, P., Gore, A., Gu, Y., Hsieh, F., Huang, X., Lee, J.H., Metz, D., Middleton, S., Mohn, D., Morgenstern, K., Morrison, M.J., Novak, P.M., Oliveira-dos-Santos, A., Powers, D., Rose, P., Schneider, S., Sell, S., Tudor, Y., Turci, S.M., Welcher, A.A., White, R.D., Zack, D., Zhao, H., Zhu, L., Zhu, X., Ghiron, C., Amouzegh, P., Ermann, M., Jenkins, J., Johnston, D., Napier, S., and Power, E., J. Med. Chem., 2006, vol. 49, p. 4981.
Di Mauro, E.F., Newcomb, J., Nunes, J.J., Bemis, J.E., Boucher, C., Chai, L., Chaffee, S.C., Deak, H.L., Epstein, L.F., Faust, T., Gallant, P., Gore, A., Gu, Y., Henkle, B., Hsieh, F., Huang, X., Kim, J.L., Lee, J.H., Martin, M.W., McGowan, D.C., Metz, D., Mohn, D., Morgenstern, K.A., Oliveira-dos-Santos, A., Patel, V.F., Powers, D., Rose, P.E., Schneider, S., Tomlinson, S.A., Tudor, Y.-Y., Turci, S.M., Welcher, A.A., Zhao, H., Zhu, L., and Zhu, X., J. Med. Chem., 2008, vol. 51, p. 1681.
Barlaam, B., Ducray, R., Lambert-van der Brempt, C., Plé, P., Bardelle, C., Brooks, N., Coleman, T., Cross, D., Kettle, J.G., and Read, J., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 2207.
Lim, J., Taoka, B., Otte, R.D., Spencer, K., Dinsmore, C.J., Altman, M.D., Chan, G., Rosenstein, C., Sharma, S., Su, H.-P., Szewczak, A.A., Xu, L., Yin, H., Zugay-Murphy, J., Marshall, C.G., Young, J.R., J. Med. Chem., 2011, vol. 54, p. 7334.
Guan, H., Lamb, M.L., Peng, B., Huang, S., DeGrace, N., Read, J., Hussain, S., Wu, J., Rivard, C., Alimzhanov, M., Bebernitz, G., Bell, K., Ye, M., Zinda, M., and Ioannidis, S., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 3105.
Ioannidis, S., Lamb, M.L., Almeida, L., Guan, H., Peng, B., Bebernitz, G., Bell, K., Alimzhanov, M., and Zinda, M., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 1669.
Marsilje, T.H., Pei, W., Chen, B., Lu, W., Uno, T., Jin, Y., Jiang, T., Kim, S., Li, N., Warmuth, M., Sarkisova, Ye., Sun, F., Steffy, A., Pferdekamper, A.-M., Li, A.G., Joseph, S.B., Kim, Y., Liu, B., Tuntland, T., Cui, X., Gray, N.S., Steensma, R., Wan, Y., Jiang, J., Chopiuk, G., Li, J., Gordon, W.P., Richmond, W., Johnson, K., Chang, J., Groessl, T., He, Y.-Q., Phimister, A., Aycinena, A., Lee, Ch.C., Bursulaya, B., Karanewsky, D.S., Seidel, H.M., Harris, J.L., and Michellys, P.-Y., J. Med. Chem., 2013, vol. 56, p. 5675.
Li, X., Zuo, Y., Tang, G., Wang, Y., Zhou, Y., Wang, X., Guo, T., Xia, M., Ding, N., and Pan, Z., J. Med. Chem., 2014, vol. 57, p. 5112.
Cervi, G., Magnaghi, P., Asa, D., Avanzi, N., Badari, A., Borghi, D., Caruso, M., Cirla, A., Cozzi, L., Felder, E., Galvani, A., Gasparri, F., Lomolino, A., Magnuson, S., Malgesini, B., Motto, I., Pasi, M., Rizzi, S., Salom, B., Sorrentino, G., Troiani, S., Valsasina, B., O’Brien, T., Isacchi, A., Donati, D., and D’Alessio, R., J. Med. Chem., 2014, vol. 57, p. 10443.
Song, Z., Yang, Y., Liu, Z., Peng, X., Guo, J., Yang, X., Wu, K., Ai, J., Ding, J., Geng, M., and Zhang, A., J. Med. Chem., 2015, vol. 58, p. 197.
Martínez González, S., Hernández, A.I., Varela, C., Rodríguez-Arístegui, S., Lorenzo, M., Rodríguez, A., Rivero, V., Martín, J.I., Saluste, C.G., Ramos-Lima, F., Cendón, E., Cebrián, D., Aguirre, E., Gomez-Casero, E., Albarrán, M., Alfonso, P., García-Serelde, B., Oyarzabal, J., Rabal, O., Mulero, F., Gonzalez-Granda, T., Link, W., Fominaya, J., Barbacid, M., Bischoff, J.R., Pizcueta, P., and Pastor, J., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 3460.
Martínez González, S., Hernández, A.I., Varela, C., Lorenzo, M., Ramos-Lima, F., Cendón, E., Cebrián, D., Aguirre, E., Gomez-Casero, E., Albarrán, M.I., Alfonso, P., García-Serelde, B., Mateos, G., Oyarzabal, J., Rabal, O., Mulero, F., Gonzalez-Granda, T., Link, W., Fominaya, J., Barbacid, M., Bischoff, J.R., Pizcueta, P., Blanco-Aparicio, C., and Pastor, J., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 5208.
Kim, J., Hong, S., and Hong, S., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 6977.
Ohwada, J., Ebiike, H., Kawada, H., Tsukazaki, M., Nakamura, M., Miyazaki, T., Morikami, K., Yoshinari, K., Yoshida, M., Kondoh, O., Kuramoto, S., Ogawa, K., Aoki, Y., and Shimma, N., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 1767.
Aliagas-Martin, I., Burdick, D., Corson, L., Dotson, J., Drummond, J., Fields, C., Huang, O.W., Hunsaker, T., Kleinheinz, T., Krueger, E., Liang, J., Moffat, J., Phillips, G., Pulk, R., Rawson, T.E., Ultsch, M., Walker, L., Wiesmann, C., Zhang, B., Zhu, B.Y., and Cochran, A.G., J. Med. Chem., 2009, vol. 52, p. 3300.
Pollard, J.R. and Mortimore, M., J. Med. Chem., 2009, vol. 52, p. 2629.
Luo, Y., Deng, Y.-Q., Wang, J., Long, Z.-J., Tu, Z.-C., Peng, W., Zhang, J.-Q., Liu, Q., and Lu, G., Eur. J. Med. Chem., 2014, vol. 78, p. 65.
Qin, W.-W., Sang, C.-Y., Zhang, L.-L., Wei, W., Tian, H.-Z., Liu, H.-X., Chen, S.-W., and Hui, L., Eur. J. Med. Chem., 2015, vol. 95, p. 174.
Lawrence, H.R., Martin, M.P., Luo, Y., Pireddu, R., Yang, H., Gevariya, H., Ozcan, S., Zhu, J.-Y., Kendig, R., Rodriguez, M., Elias, R., Cheng, J.Q., Sebti, S.M., Schonbrunn, E., and Lawrence, N.J., J. Med. Chem., 2012, vol. 55, p. 7392.
Curtin, M.L., Heyman, H.R., Frey, R.R., Marcotte, P.A., Glaser, K.B., Jankowski, J.R., Magoc, T.J., Albert, D.H., Olson, A.M., Reuter, D.R., Bouska, J.J., Montgomery, D.A., Palma, J.P., Donawho, C.K., Stewart, K.D., Tse, C., and Michaelides, M.R., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 4750.
Cee, V.J., Schenkel, L.B., Hodous, B.L., Deak, H.L., Nguyen, H.N., Olivieri, Ph.R., Romero, K., Bak, A., Be, X., Bellon, S., Bush, T.L., Cheng, A.C., Chung, G., Coats, S., Eden, P.M., Hanestad, K., Gallant, P.L., Gu, Y., Huang, X., Kendall, R.L., Lin, M.-H.J., Morrison, M.J., Patel, V.F., Radinsky, R., Rose, P.E., Ross, S., Sun, J.-R., Tang, J., Zhao, H., Payton, M., and Geuns-Meyer, S.D., J. Med. Chem., 2010, vol. 53, p. 6368.
Kamal, A., Dastagiri, D., Ramaiah, M.J., Reddy, J.S., Bharathi, E.V., Reddy, M.K., Sagar, M.V.P., Reddy, T.L., Pushpavalli, S.N.C.V.L., and Pal-Bhadra, A., Eur. J. Med. Chem., 2011, vol. 46, p. 5817.
Shao, H., Shi, Sh., Foley, D.W., Lam, F., Abbas, A.Y., Liu, X., Huang, Sh., Jiang, X., Baharin, N., Fischer, P.M., and Wang, Sh., Eur. J. Med. Chem., 2013, vol. 70, p. 447.
Bryan, M.C., Falsey, J.R., Frohn, M., Reichelt, A., Yao, G., Bartberger, M.D., Bailis, J.M., Zalameda, L., Miguel, T.S., Doherty, E.M., and Allen, J.G., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2056.
Woods, K.W., Lai, Ch., Miyashiro, J.M., Tong, Y., Florjancic, A.S., Han, E.K., Soni, N., Shi, Y., Lasko, L., Leverson, J.D., Johnson, E.F., Shoemaker, A.R., and Penning, T.D., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 1940.
Shao, H., Shi, S., Huang, S., Hole, A.J., Abbas, A.Y., Baumli, S., Liu, X., Lam, F., Foley, D.W., Fischer, P.M., Noble, M., Endicott, J.A., Pepper, C., and Wang, S., J. Med. Chem., 2013, vol. 56, p. 640.
Vasbinder, M.M., Aquila, B., Augustin, M., Chen, H., Cheung, T., Cook, D., Drew, L., Fauber, B.P., Glossop, S., Grondine, M., Hennessy, E., Johannes, J., Lee, S., Lyne, P., Mörtl, M., Omer, C., Palakurthi, S., Pontz, T., Read, J., Sha, L., Shen, M., Steinbacher, S., Wang, H., Wu, A., Ye, M., J. Med. Chem., 2013, vol. 56, p. 1996.
Kim, S., Jung, J.K., Lee, H.S., Kim, Y., Kim, J., Choi, K., Baek, D.J., Moon, B., Oh, K.S., Lee, B.H., Shin, K.J., Pae, A.N., Nam, G., Roh, E.J., Cho, Y.S., and Choo, H., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 3002.
Zificsak, C.A., Theroff, J.P., Aimone, L.D., Albom, M.S., Angeles, T.S., Brown, R.A., Galinis, D., Grobelny, J.V., Herbertz, T., Husten, J., Kocsis, L.S., LoSardo, C., Miknyoczki, S.J., Murthy, S., Rolon-Steele, D., Underiner, T.L., Wells-Knecht, K.J., Worrell, C.S., Zeigler, K.S., and Dorsey, B.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 660.
Weinberg, L.R., Albom, M.S., Angeles, T.S., Husten, J., Lisko, J.G., McHugh, R.J., Milkiewicz, K.L., Murthy, S., Ott, G.R., Theroff, J.P., Tripathy, R., Underiner, T.L., Zificsak, C.A., and Dorsey, B.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 164.
Zhou, N., Moradei, O., Raeppel, S., Leit, S., Frechette, S., Gaudette, F., Paquin, I., Bernstein, N., Bouchain, G., Vaisburg, A., Jin, Z., Gillespie, J., Wang, J., Fournel, M., Yan, P.T., Trachy-Bourget, M.C., Kalita, A., Lu, A., Rahil, J., MacLeod, A.R., Li, Z., Besterman, J.M., and Delorme, D., J. Med. Chem., 2008, vol. 51, p. 4072.
Paris, M., Porcelloni, M., Binaschi, M., and Fattori, D., J. Med. Chem., 2008, vol. 51, p. 4072.
Lavoie, R., Bouchain, G., Frechette, S., Woo, S.H., Abou-Khalil, E., Leit, S., Fournel, M., Yan, P.T., Trachy-Bourget, M.-C., Beaulieu, C., Li, Z., Besterman, J., and Delorme, D., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2847.
Woo, S.H., Frechette, S., Abou-Khalil, E., Bouchain, G., Vaisburg, A., Bernstein, N., Moradei, O., Leit, S., Allan, M., Fournel, M., Trachy-Bourget, M.-C., Li, Z., Besterman, J., and Delorme, D., J. Med. Chem., 2002, vol. 45, p. 2877.
Bouchain, G., Leit, S., Frechette, S., Abou-Khalil, E., Lavoie, R., Moradei, O., Woo, S.-H., Fournel, M., Yan, P.T., Kalita, A., Trachy-Bourget, M.-C., Beaulieu, C., Li, Z., Robert, M.-F., MacLeod, A.R., Besterman, J.M., and Delorme, D., J. Med. Chem., 2003, vol. 46, p. 820.
Vaisburg, A., Bernstein, N., Frechette, S., Allan, M., Abou-Khalil, E., Leit, S., Moradei, O., Bouchain, G., Wang, J., Woo, S.H., Fournel, M., Yan, P.T., Trachy-Bourget, M.-C., Kalita, A., Beaulieu, C., Li, Z., MacLeod, R., Besterman, J.M., and Delorme, D., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 283.
Raeppel, S., Gaudette, F., Paquin, I., Vaisburg, A., and Delorme, D., WO Patent no. 035525, 2004.
Fournel, M., Bonfils, C., Hou, Y., Yan, P.T., Trachy-Bourget, M.-C., Kalita, A., Liu, J., Lu, A.-H., Zhou, N.Z., Robert, M.-F., Gillespie, J., Wang, J.J., Ste-Croix, H., Rahil, J., Lefebvre, S., Moradei, O., Delorme, D., MacLeod, A.R., Besterman, J.M., and Li, Z., Mol. Cancer Ther., 2008, vol. 7, p. 759.
Ignatovich, Zh.V., Sinyutich, Yu.V., Gusak, K.N., and Koroleva, E.V., Russ. J. Org. Chem., 2015, vol. 51, p. 1449.
Koroleva, E.V., Ignatovich, Zh.V., Gusak, K.N., Ermolinskaya, A.L., and Sinyutich, Yu.V., Russ. J. Org. Chem., 2015, vol. 51, p. 101.
Rajak, H., Agarawal, A., Parmar, P., Thakur, B.S., Veerasamy, R., Sharma, P.Ch., and Kharya, M.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 5735.
Morphy, R., J. Med. Chem., 2010, vol. 53, p. 1413.
Bansal, Y. and Silakari, O., Eur. J. Med. Chem., 2014, vol. 53, p. 31.
Posy, Sh.L., Hermsmeier, M.A., Vaccaro, W., Ott, K.-H., Todderud, G., Lippy, J.S., Trainor, G.L., Loughney, D.A., and Johnson, S.R., J. Med. Chem., 2011, vol. 54, p. 54.
Huggins, D.J., Sherman, W., and Tidor, B., J. Med. Chem., 2012, vol. 55, p. 1424.
Noble, M.E.M., Endicott, J.A., and Johnson, L.N., Science, 2004, vol. 303, p. 1800.
Bamborough, P., Brown, M.J., Christopher, J.A., Chung, Ch., and Mellor, G.W., J. Med. Chem., 2011, vol. 54, p. 5131.
Bikker, J.A., Brooijmans, N., Wissner, A., and Mansour, T.S., J. Med. Chem., 2009, vol. 52, p. 1493.
Shah, N.P., Tran, C., Lee, F.Y., Chen, P., Norris, D., and Sawyers, C.L., Science, 2004, vol. 305, p. 399.
Giroux, S., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 394.
Mahboobi, S., Dove, S., Sellmer, A., Winkler, M., Eichhorn, E., Pongratz, H., Ciossek, T., Baer, T., Maier, T., and Beckers, T., J. Med. Chem., 2009, vol. 52, p. 2265.
El-Deeb, I.M. and Lee, S.H., Bioorg. Med. Chem., 2010, vol. 18, p. 3860.
Lü, Sh., Luo, Q., Hao, X., Li, X., Ji, L., Zheng, W., and Wang, F., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 6964.
Hudkins, R.L., Becknell, N.C., Zulli, A.L., Underiner, T.L., Angeles, T.S., Aimone, L.D., Albom, M.S., Chang, H., Miknyoczki, S.J., Hunter, K., Jones-Bolin, S., Zhao, H., Bacon, E.R., Mallamo, J.P., Ator, M.A., and Ruggeri, B.A., J. Med. Chem., 2012, vol. 55, p. 903.
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Original Russian Text © E.V. Koroleva, Zh.I. Ignatovich, Yu.V. Sinyutich, K.N. Gusak, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 2, pp. 159–196.
Elena Vadimovna Koroleva was born in 1946 in Brest, BSSR. Doctor of chemical sciences, principal researcher of the Institute of New Materials Chemistry, National Academy of Sciences of Belarus. She graduated from the chemical faculty of the Saint-Petersburg (Leningrad) State University in 1968, she was the disciple of Professor B.V. Ioffe. Candidate of chemical sciences since 1974, Doctor of chemical sciences since 1998.
Field of scientific interests: chemistry of heterocyclic compounds of pyrimidine, quinoline, isoxazole, fine organic synthesis.
Zhanna Vladimirovna Ignatovich was born in 1971in Prosvet township, Volzhskii region, Kuibyshev oblast. Candidate of chemical sciences (2010), leading researcher of the Institute of New Materials Chemistry, National Academy of Sciences of Belarus. She graduated from the chemical faculty of the Belorussian State University in 1997.
Field of scientific interests: organic synthesis of heterocyclic compounds.
Yuliya Vyacheslavovna Sinyutich was born in 1989 in Postavy town, Belarus Republic. Post-graduate student of the Institute of New Materials Chemistry, National Academy of Sciences of Belarus. She graduated from the chemical faculty of the Belorussian State University in 2012, Master of chemistry (2013).
Field of scientific interests: chemistry of heterocyclic compounds.
Klavdiya Nikolaevna Gusak was born in 1950 in Shereshevo township, Pruzhanskii region, Brest oblast, BSSR. Candidate of chemical sciences (1981), senior researcher of the Institute of New Materials Chemistry, National Academy of Sciences of Belarus. She graduated from the chemical faculty of the Belorussian State University in 1972.
Field of scientific interests: chemistry of heterocyclic compounds, multicomponent reactions in organic synthesis.
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Koroleva, E.V., Ignatovich, Z.I., Sinyutich, Y.V. et al. Aminopyrimidine derivatives as protein kinases inhibitors. Molecular design, synthesis, and biologic activity. Russ J Org Chem 52, 139–177 (2016). https://doi.org/10.1134/S1070428016020019
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DOI: https://doi.org/10.1134/S1070428016020019