PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Alkaloidy kory chinowej : małe cząsteczki, które wiele mogą

Treść / Zawartość
Identyfikatory
Warianty tytułu
EN
Cinchona alkaloids : small hardworkers
Języki publikacji
PL
Abstrakty
EN
Cinchona alkaloids comprising quinine, quinidine, cinchonidine and cinchonine as the major members constitute a unique class of quinoline alkaloids with tremendous impact on human civilization (Section 1). The odyssey of Cinchona alkaloids began with the discovery of their antimalarial properties followed by antiarrhytmic action of quinidine. Currently medicinal chemistry of Cinchona alkaloids derivatives develops rapidly and many other activities such as cytotoxic, multidrug resistance inhibitory have been demonstrated (Section 5) [5]. Beside medicine Cinchona alkaloids gave also the fundaments of stereochemistry and asymmetric synthesis. An extraordinary catalytic potency of parent and modified Cinchona alkaloids (deserving privileged catalyst classification) include more than 50 types of diverse stereoselective reactions, with few spectacular such as asymmetric dihydroxylation of alkenes or heterogeneous α-ketoesters hydrogenation (Section 3) [3]. Last but not least the portfolio of applications of Cinchona alkaloids includes resolution of racemates by diastereomeric crystallization or by the use of Cinchona- -based chiral stationary phases for ion-exchange enantioselective chromatography and other recognition or sensing systems (Section 4) [166]. Easy transformation of Cinchona alkaloids (for example by click chemistry) into other chiral and modular building blocks together with current pressure on a more intense exploration of sustainable products make cinchona alkaloids of primary importance for modern synthetic, catalytic and medicinal chemistry. The aim of this review which covers over 200 references is to briefly summarize all aspects of Cinchona alkaloid chemistry and biology with the special emphasis on new applications.
Rocznik
Strony
443--493
Opis fizyczny
Bibliogr. 233 poz., rys., schem.
Twórcy
autor
  • Wydział Chemii UAM ul. Umultowska 89B, 61-614 Poznań
autor
  • Wydział Chemii UAM ul. Umultowska 89B, 61-614 Poznań
Bibliografia
  • [1] P. LeCouteur, J. Burreson, Guziki Napoleona. Jak 17 cząsteczek zmieniło historię, Wyd. Twoj Styl, Warszawa 2004.
  • [2] T.P. Yoon, E.N. Jacobsen, Science, 2003, 299, 1691.
  • [3] Cinchona Alkaloids in Synthesis&Catalysis, Ch.E. Song (red.), Wiley-VCH Weinheim 2009.
  • [4] F. Eiden, F. Pharmazie in unserer Zeit, 1998, 27, 257, ibid. 1999, 28, 11 ibid. 1999, 28, 74.
  • [5] K. Kacprzak, Chemistry and Biology of Cinchona alkaloids and Its Derivatives [w:] Handbook of Natural Products – Phytochemistry, Botany, Metabolism, K.G. Ramawat, J.-M. Merillon, (red.), Springer 2013.
  • [6] Casteel DA (1997) Antimalarial Agents, [w:] Burger’s Medicinal Chemistry and Drug Discovery 5, Wolff ME (red.), J. Wiley & Sons, New York, str. 3.
  • [7] D.V. McCalley, Analyst, 1990, 115, 1355.
  • [8] J.M. Karle, I.L. Karle, L. Gerena, W.K. Milhous, Antimicrob. Agents Chemother., 1992, 36, 1538.
  • [9] S. Krishna, N.J. White, Clin. Pharmacokinet., 1996, 30, 263.
  • [10] A.A. Grace, J. Camm, New Engl. J. Med., 1998, 338, 35.
  • [11] J. Pelletier, J.B. Caventou, Ann. Chim. Phys., 1820, 14, 69., ibid. 1820, 15, 291; ibid. 1820, 15, 337.
  • [12] A. Delondre, H. Henry, J. Pharm., 1833, 19, 623; ibid. 1834, 20, 157.
  • [13] F.L. Winckler, Jahresbericht 1847, 620.
  • [14] J.G. Díaz, J.G. Sazatornil, M.L. Rodríguez, L.R. Mesía, G.V. Arana, J. Nat. Prod., 2004, 67, 1667.
  • [15] G. Trier, G.W. Die Alkaloide, Ed. Verlag Borntraeger: Berlin, 1931, 399.
  • [16] R.B. Turner, R.B. Woodward, The Alkaloids, tom III, R.H.F. Manske, H.L. Holmes (red.) Academic Press, New York 1953, str. 24.
  • [17] J.P. Michael, The Quinoline Alkaloids, [w:] Rodd’s Chemistry of Carbon Compounds, Wyd. 2, 2nd Suppl., tom IV, F.G. Part., M. Sainsbury (red.), Elsevier, Amsterdam, 1998, str. 432.
  • [18] P. Rabe, E. Ackerman, W. Schneider, Ber., 1907, 40, 3655; ibid. 1908, 41, 62.
  • [19] V. Prelog, E. Zalan, Helv. Chim. Acta, 1944, 27, 535; ibid. 1944, 27, 545, ibid. 1950, 33, 2021.
  • [20] T.S. Kaufman, E.A. Ruvedaang, Angew. Chem. Int. Ed., 2005, 44, 854.
  • [21] P. Rabe, K. Kindler, Ber., 1918, 51, 466.
  • [22] R.B. Woodward, W. E. Doering, J. Am. Chem. Soc., 1944, 66, 849.
  • [23] A.C. Smith, R.M. Williams, Angew. Chem. Int. Ed., 2008, 47, 1736.
  • [24] J.I. Seeman, Angew. Chem. Int. Ed., 2007, 46, 1378.
  • [25] M.R. Uskokovic, T. Henderson, C. Reese, H.L. Lee, G. Grethe, J. Gutzwiller, J. Am. Chem. Soc., 1978, 100, 571.
  • [26] J. Gutzwiller, M.R. Uskokovic, J. Am. Chem. Soc., 1978, 100, 576.
  • [27] G. Grethe, H.S. Lee, T. Mitt, M.R. Uskokovic, J. Am. Chem. Soc., 1978, 100, 581.
  • [28] G. Grethe, H.S. Lee, T. Mitt, M.R. Uskokovic, J. Am. Chem. Soc., 1978, 100, 589.
  • [29] G. Stork, D. Niu, R.A. Fujimoto, E.R. Koft, J.M. Balkovec, J.R. Tata, G.R. Dake, J. Am. Chem. Soc., 2001, 123, 3239.
  • [30] I.T. Raheem, S.N. Goodman, E.N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 706. 488 K. Kacprzak, P. Czarnecki
  • [31] J. Igarashi, M. Katsukawa, Y.G. Wang, H.P. Acharya, Y. Kobayashi, Tetrahedron Lett., 2004, 45, 3783.
  • [32] L. Pasteur, Compt. Rend. Acad. Sci., 1853, 37, 110, 162.
  • [33] G. Bredig, P.S. Fiske, Biochem. Z., 1912, 46, 7.
  • [34] H. Pracejus, Liebigs Ann. Chem., 1960, 634, 9.
  • [35] R.A. Johnson, K.B. Sharpless, Catalytic Asymmetric Dihydroxylation – Discovery and Development, [w:] Catalytic Asymmetric Synthesis; Wyd. 2, I. Ojima (red.), Wiley-VCH, New York, 2000, rozdział 6D; 357.
  • [36] C. Bolm, J.P. Hildebrand, K. Muniz, Recent Advances in AD and AA, ibid. rozdział 6E; 399.
  • [37] I.E. Marko, J.S. Svendsen, Dihydroxylation of Carbon-Carbon Double Bond, [w:] Comprehensive Asymmetric Catalysis, E.N. Jacobsen, A. Pfaltz, H. Yamamoto (red.), Springer, Berlin, 1999, str. 713.
  • [38] K.B. Sharpless, [w:] Transition Metal for Organic Synthesis, M. Beller, C. Bolm (Red.), tom. 2, Wiley-VCH, Weinheim 1998, str. 219.
  • [39] H.C. Kolb, M.S. Van Nieuwenhze, K.B. Sharpless, Chem. Rev., 1994, 94, 2483.
  • [40] M.J. O’Donnel, Asymmetric Phase Transfer Reactions, [w:] Catalytic Asymmetric Synthesis, Wyd. 2, I. Ojima (red.), Wiley-VCH, Nowy Jork 2000, str. 727.
  • [41] S.-S. Jew, H.-G. Park, Chem. Commun., 2009, 7090.
  • [42] T. Marcelli, R.N.S. van der Haas, J.H. van Maarseveen, H. Hiemstra, Angew. Chem. Int. Ed., 2006, 45, 929.
  • [43] T. Marcelli, J.H. van Maarseveen, H. Hiemstra, Angew. Chem. Int. Ed., 2006, 45, 7496.
  • [44] S.J. Connon, Chem. Commun., 2008, 2499.
  • [45] P. Newman, Optical Resolution Procedures for Chemical Compounds, Tom 2, Acids, Optical Resolution Information Center, Manhattan College, Riverdale, Nowy Jork 1981, str. 7.
  • [46] J. Jacques, A. Collet, S.H. Wilen, Enantiomers, Racemates and Resolutions, Wiley, Nowy Jork 1981, 254, str. 257.
  • [47] R.A. Sheldon, Chirotechnology, Marcel Dekker, Nowy Jork 1993, rozdział 6.
  • [48] Chirality in Industry, Tom 1, 2, A.N. Collins, G.N. Sheldrake, J. Crosby (red.), Wiley, Chichester 1992, str. 1997.
  • [49] R. Verpoorte, J. Schripsema, T. Van der Leer, [w:] The Alkaloids. Chemistry and Pharmacology, A. Brossi (red.), Academic Press, Nowy Jork 1988, 34.
  • [50] C. Palacio, S.J. Connon, Org. Lett., 2011, 13, 1298.
  • [51] L. Hintermann, M. Schmitz, U. Englert, Angew. Chem. Int. Ed., 2007, 46, 5164.
  • [52] M. Baidya, M. Horn, H. Zipse, H. Mayr, J. Org. Chem., 2009, 74, 7157.
  • [53] H. Hiemstra, H. Wynberg, J. Am. Chem. Soc., 1981, 103, 417.
  • [54] R. Hubel, K. Polborn, W. Beck, Eur. J. Inorg. Chem., 1999, 471.
  • [55] C. Missling, S. Mihan, K. Polborn, W. Beck, Chem. Ber., 1996, 129, 331.
  • [56] H.C. Kolb, P.G. Anderson, K.B. Sharpless, J. Am. Chem. Soc., 1994, 116, 1278.
  • [57] E.J. Corey, M.C. Noe, J. Am. Chem. Soc., 1996, 118, 11038.
  • [58] E.J. Corey, M.C. Noe, J. Am. Chem. Soc., 1996, 118, 319.
  • [59] R.M. Dijkstra, H. Kellog, H. Wynberg, J.S. Svendsen, I. Marko, K.B. Sharpless, J. Am. Chem. Soc., 1989, 111, 8069.
  • [60] G.D.H. Dijkstra, R.M. Kellog, H. Wynberg, J. Org. Chem., 1990, 55, 6121.
  • [61] S. Kashino, M. Haisa, Acta Cryst., 1983, C39, 310.
  • [62] B. Oleksyn, Acta Cryst., 1982, B38, 1832.
  • [63] B. Oleksyn, Ł Lebioda, M. Ciechanowicz-Rutkowska, Acta Cryst., 1979, B35, 440.
  • [64] L. Dupond, A. Konsur, K. Lewiński, B. Oleksyn, Acta Cryst., 1985, C41, 616.
  • [65] T. Burgi. A. Baiker, J. Am. Chem. Soc., 1998, 120, 12920.
  • [66] M. Aune, A. Gogoll, O. Matsson, O.J. Org. Chem., 1995, 60, 1356.
  • [67] E.J. Corey, M.C. Noe, S. Sarshar, Tetrahedron Lett., 2004, 35, 2861.
  • [68] W. Amberg Y.L. Bennani, R.K. Chadha, G.A. Crispino, W.D. Davis, J. Hartung, K.S. Jeong, Y. Ogino, T. Shibata, K.B. Sharpless, J. Org. Chem., 1993, 58, 844.
  • [69] H. Li, X. Liu, F. Wu, L. Tang, L. Deng, Proc. Nat. Acad. Sci. USA, 2010, 107, 20625.
  • [70] S. Kristyan, J. Phys. Chem. C, 2009, 113, 21700.
  • [71] A. Vargas, D. Ferri, N. Bonalumi, T. Mallat, A. Baiker, Angew. Chem. Int. Ed., 2007, 46, 3905.
  • [72] M. Meldal, C.W. Tornoe, Chem. Rev., 2008, 108, 2952.
  • [73] K. Kacprzak, Wiad. Chem., 2005, 59, 584.
  • [74] W.M. Braje, J. Frackenpohl, O. Schrake, R. Wartchow, W. Beil, H.M.R. Hoffmann, Helv. Chim. Acta, 2000, 83, 777.
  • [75] K.M. Kacprzak, W. Linder, N.M. Maier, Chirality, 2008, 20, 441.
  • [76] H. Brunner, J. Bugler, B. Nuber, Tetrahedron: Asymmetry, 1995, 6, 1699.
  • [77] S. Roper, M.H. Franz, R. Wartchow, H.M.R. Hoffmann, Org. Lett., 2003, 5, 2773.
  • [78] K. Kacprzak, B. Gierczyk, Tetrahedron: Asymmetry, 2010, 21, 2740.
  • [79] K. Kacprzak, M. Migas, A. Plutecka, U. Rychlewska, J. Gawroński, Heterocycles, 2005, 65, 1931.
  • [80] K. Koczajewska, praca magisterska Wydział Chemii UAM, Poznań 2012.
  • [81] B. Baraniak, K. Kacprzak, L. Celewicz, Bioorg. Med. Chem. Lett., 2011, 21, 723.
  • [82] K. Kacprzak, Synlett, 2005, 943.
  • [83] K.M. Kacprzak, N.M. Maier, W. Lindner, Tetrahedron Lett., 2006, 47, 8721.
  • [84] H. Pracejus, Fortschr. Chem. Forsch., 1967, 8, 493.
  • [85] Ch.E. Hoyle, Ch.N. Bowman, Angew. Chem. Int. Ed., 2010, 49, 1540.
  • [86] H. Wynberg, Topics in Stereochemistry, 1986, 16, 87.
  • [87] K. Kacprzak, J. Gawroński, Synthesis, 2001, 961.
  • [88] H. Hiemstra, T. Marcelli, Synthesis, 2010, 1229.
  • [89] H. Wynberg, E.G.J. Staring, J. Am. Chem. Soc., 1982, 104, 166.
  • [90] R. Tennyson, D. Romo, J. Org. Chem., 2000, 65, 7248.
  • [91] A.E. Taggi, H. Wack, A.M. Hafez, S. France, T. Lectka, Org. Lett., 2002, 4, 627.
  • [92] P. Stutte, The Preparation and Uses of Enantiomerically Pure β-Lactones, [w:] Chirality in Industry, tom 1, A.N. Collins, G.N. Sheldrake, J. Crosby (red.), Wiley, Chichester 1992, str. 341.
  • [93] C.E. Song, J.K. Lee, S.H. Lee, S. Lee, Tetrahedron: Asymmetry, 1995, 6, 1063.
  • [94] C.E. Song, J.K. Lee, I. O’Kim, J.H. Choi, Synt. Commun., 1997, 27, 1009.
  • [95] P.E.F. Ketelaar, E.G.J. Staring, H. Wynberg, Tetrahedron Lett., 1985, 26, 4665.
  • [96] R.L. Tennyson, G.S. Cortez, H.J. Galicia, Ch.R. Kreiman, Ch.M. Thompson, D. Romo, Org. Lett., 2002, 4, 533.
  • [97] T. Fujisawa, T. Ito, K. Fujimoto, M. Shimizu, H. Wynberg, E.G.J. Staring, Tetrahedron Lett., 1997, 38, 1593.
  • [98] E.G.J. Staring, H. Moorlag, H. Wynberg, Recl. Trav. Chim. Pays-Bas, 1986, 105, 374.
  • [99] R.R.L. Tennyson, G.S. Cortez, H.J. Galicia, C.R. Kreiman, C.M. Thompson, D. Romo, Org. Lett., 2002, 4, 533.
  • [100] H. Hiemstra, H. Wynberg, J. Am. Chem. Soc., 1981, 103, 417.
  • [101] U-H. Dolling, P. Davis, E.J.J. Grabowski, J. Am. Chem. Soc., 1984, 106, 446.
  • [102] B. Lygo, P.G. Wainwright, Tetrahedron Lett., 1997, 38, 8595.
  • [103] E.J. Corey, F. Xu, M.C. Noe, J. Am. Chem. Soc., 1997, 119, 12414.
  • [105] M.J. O’Donnell, Aldrichimica Acta, 2001, 34, 3.
  • [106] M.J. O’Donnell, S. Wu, J.C. Huffman, Tetrahedron, 1994, 50, 4507.
  • [107] E.J. Corey, M.C. Noe, F. Xu, Tetrahedron Lett., 1998, 39, 5347.
  • [108] F.-Y. Zhang, E.J. Corey, Org. Lett., 2000, 2, 1097.
  • [109] T. Perrard, J.-Ch. Plaquevent, J.-R. Desmurs, D. Hebrault, D. Org. Lett., 2000, 2, 2959.
  • [110] E.N. Jacobsen, I. Marko, M.B. France, J.S. Svendsen, K.B. Sharpless, J. Am. Chem. Soc., 1989, 111, 737.
  • [111] J.S.M. Wai, I. Marko, J.S. Svendsen, M.G. Finn, E.N. Jacobsen, K.B. Sharpless, J. Am. Chem. Soc., 1989, 111, 1123.
  • [112] K.B. Sharpless, W. Amberg, M. Beller, H. Chen, J. Hartung, Y. Kawanami, D. Lubben, E. Manoury, Y. Ogino, T. Shibata, T. Ukita, J. Org. Chem., 1991, 56, 4585.
  • [113] K.B. Sharpless, W. Amberg, Y.L. Bennani, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem., 1992, 57, 2768.
  • [114] G.A. Crispino, K.-S. Jeong, H.C. Kolb, Z.-M. Wang, D. Xu, K.B. Sharpless, J. Org. Chem., 1993, 58, 3785.
  • [115] H. Becker, S.B. King, M. Taniguchi, K.P.M. Vanhessche, K.B. Sharpless, J. Org. Chem., 1995, 60, 3940.
  • [116] H. Becker, K.B. Sharpless, Angew. Chem. Int. Ed., 1996, 35, 448.
  • [117] L. Wang, K.B. Sharpless, J. Am. Chem. Soc., 1992, 114, 7568.
  • [118] Y. Orito, S. Imai, S. Niwa, G.-H. Nguyen, J. Synt. Org. Chem. Jpn., 1979, 37, 173.
  • [119] Y. Orito, S. Imai, S. Niwa, J. Chem. Soc. Jpn., 1979, 1118.
  • [120] H.-U. Blaser, M. Garland, J. Am. Chem. Soc., 1990, 112, 7048.
  • [121] W. He, P. Liu, B.L. Zhang, S.L. Sun, S.Y. Zhang, App. Organomet. Chem., 2006, 20, 328.
  • [122] W. He, B.-L. Zhang, R. Jiang, P. Liu, X.-L. Sun, S.-Y. Zhang, Tetrahedron Lett., 2006, 47, 5367.
  • [123] M. Studer, S. Burkhardt, A. . Indolese, H.-U. Blaser, Chem. Commun., 2000, 1327.
  • [124] P. Herold, A.F. Indolese, M. Studer, H.P. Jalett, U. Siegrist, H.-U. Blaser, Tetrahedron, 2000, 56, 6497.
  • [125] A. Baiker, H.U. Blaser, Cinchona-Modified Platinum Hydrogenation Catalysts and Related Systems [w:] Handbook of Heterogeneous Catalysis, G. Ertl G, H. Knozinger, J. Weitkamp (red.), VCH: Weinheim 1997, 2425.
  • [126] Y.-C. Chen, Synlett, 2008, 1919.
  • [127] L.-W. Xu, J. Luo, Y. Lu, Chem. Commun., 2009, 1807.
  • [128] B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, L. He, Org. Biomol. Chem., 2007, 5, 2913.
  • [129] J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. Int. Ed., 2008, 47, 7656.
  • [130] G. Bencivennia, P. Galzerano, A. Mazzantia, G. Bartolia, P. Melchiorre, Proc. Nat. Acad. Sci., 2010, 107, 20642.
  • [131] W. Sun, L. Hong, C. Liu, R. Wang, Tetrahedron: Asymmetry, 2010, 21, 2493.
  • [132] O. Lifchits, C.M. Reisinger, B. List, J. Am. Chem. Soc., 2010, 132, 10227.
  • [133] D. Ding, C.-G. Zhao, Eur. J. Org. Chem., 2010, 20, 3802.
  • [134] T. Zweifel, D. Hollmann, B. Pruger, M. Nielsen, K.A. Jorgensen, Tetrahedron: Asymmetry, 2010, 21, 1624.
  • [135] E. Zhang, C.-A. Fan, T.-Q. Tu, F.-M. Zhang, Y.-L. Song, J. Am. Chem. Soc., 2009, 131, 14626.
  • [136] F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. Int. Ed., 2008, 47, 8703.
  • [137] B. Vakulya, S.Varga, A. Csampai, T. Soos, Org. Lett. 2005, 7, 1967.
  • [138] S.H. McCooey, S.J. Connon, Angew. Chem. Int. Ed. 2005, 44, 6367.
  • [139] J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun., 2005, 4481.
  • [140] M. Markert, M. Mulzer, B. Schetter, R. Mahrwald, J. Am. Chem. Soc., 2007, 129, 7258.
  • [141] B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, L. He, Org. Biomol. Chem., 2007, 5, 2913.
  • [142] J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. Int. Ed., 2008, 47, 7656.
  • [143] J.R. Chen, X.L. An, X.Y. Zhu, X.F. Wang, W.J. Xiao, J. Org. Chem., 2008, 73, 6006.
  • [144] J. Ye, D.J. Dixon, P. Hynes, Chem. Commun., 2005, 4481.
  • [145] A.E. Mattson, A.M. Zuhl, T.E. Reynolds, K.A. Scheidt, J. Am. Chem. Soc., 2006, 128, 4932.
  • [146] J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc., 2006, 128, 6048.
  • [147] L. Bernardi, F. Fini, R.P. Herrera, A. Ricci, V. Sgarzani, Tetrahedron, 2006, 62, 375.
  • [148] A. Berkessel, S. Mukherjee, T.N. Mueller, F. Cleemann, K. Roland, M. Brandenburg, J.-M. Neudoerfl, J. Lex, Org. Biomol. Chem., 2006, 4, 4319.
  • [149] A.L. Tillman, J. Ye, D.J. Dixon, Chem. Commun., 2006, 1191.
  • [150] J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc., 2006, 128, 12652.
  • [151] Y.-Q. Wang, J. Song, R. Hong, H. Li, L. Deng, J. Am. Chem. Soc., 2006, 128, 8156.
  • [152] B. Vakulya, S. Varga, T. Soós, J. Org. Chem., 2008, 73, 3475.
  • [153] F. Wang, X. Liu, X. Cui, Y. Xiong, X. Zhou, X. Feng, Chem. Eur. J., 2009, 15, 589.
  • [154] J. Aleman, A. Milelli, S. Cabrera, E. Reyes, K.A. Jorgensen, Chem. Eur. J., 2008, 14, 10958.
  • [155] C. Gioia, A. Hauville, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. Int. Ed., 2008, 47, 9236.
  • [156] M.M. Biddle, M. Lin, K.A. Scheidt, J. Am. Chem. Soc., 2007, 129, 3830.
  • [157] J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc., 2006, 128, 6048.
  • [158] P.S. Hynes, P.A. Stupple, D.J. Dixon, Org. Lett., 2008, 10, 1389.
  • [159] P. Li, S. Wen, F. Yu, Q. Liu, W. Li, Y. Wang, X. Liang, J. Ye, Org. Lett., 2009, 11, 753.
  • [160] J.-R. Chen, X.-L. An, X.-Y. Zhu, X.-F. Wang, W.-J. Xiao, J. Org. Chem., 2008, 73, 6006.
  • [161] J.-R. Chen, Y.-J. Cao, Y.-Q. Zou, F. Tan, L. Fu, X.-Y. Zhu, W.-J. Xiao, Org. Biomol. Chem., 2010, 8, 1275.
  • [162] WO 2011/028309 A1.
  • [163] P.M. Pihko, I. Majander, A. Erkkila, Top. Curr. Chem., 2010, 291, 29.
  • [164] S. Mukherjee, J.W. Yang, S. Hoffmann, B. List, Chem. Rev., 2007, 107, 5471.
  • [165] P. Czarnecki, A. Plutecka, J. Gawroński, K. Kacprzak, Green Chem., 2011, 13, 1280.
  • [166] K. Kacprzak, K. Gawroński, Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives [w:] Cinchona Alkaloids in Synthesis&Catalysis, Ch.E. Song (red.), Wiley-VCH, Weinheim 2009, 421.
  • [167] J. Reeder, P.P. Castro, C.B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem., 1994, 59, 3151.
  • [168] K. Ding, Y. Wang, H. Yun, J. Liu, Y. Wu, M. Terada, Y. Okubo, K. Mikami, Chem. Eur. J., 1999, 5, 1734.
  • [169] D.W. Cai, D.L. Hughes, T.R. Verhoeven, P.J. Reider, Tetrahedron Lett., 1995, 36, 7991.
  • [170] Q.S. Hu, D. Vitharana, L. Pu, Tetrahedron: Asymmetry, 1995, 6, 2123.
  • [171] Y. Wang, J. Sun, K. Ding, Tetrahedron, 2000, 56, 4447.
  • [172] C. Rosini, C. Bertucci, D. Pini, P. Altemura, P. Salvadori, Tetrahedron Lett., 1985, 26, 3361.
  • [173] P. Salvadori, D. Pini, C. Rosini, C. Bertucci, G. Uccello-Barretta, Chirality, 1992, 4, 43.
  • [174] M. Lammerhofer, W. Lindner, J. Chrom. A, 1996, 741, 33.
  • [175] A. Mandl, L. Nicoletti, M. Lammerhofer, W. Lindner, J. Chrom. A, 1999, 858, 1.
  • [176] M. Lammerhofer, N.M. Maier, W. Lindner, WO 97/46557, 1997.
  • [177] M. Lammerhofer, N.M. Maier, W. Lindner, Am. Lab., 1998, 30, 71.
  • [178] M. Lammerhofer, W. Lindner, Adv. Chrom., 2008, 46, 1.
  • [179] N.M. Maier, S. Schefzick, G.M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K.B. Lipkowitz, J. Am. Chem. Soc., 2002, 124, 8611.
  • [180] B. Gavioli, N.M. Maier, C. Minguillón, W. Lindner, Anal. Chem., 2004, 76, 5837.
  • [181] C. Czerwenka, M.M. Zhang, H. Kahlig, N.M. Maier, K.B. Lipkowitz, W. Lindner, J. Org. Chem., 2003, 68, 8315.
  • [182] C. Czerwenka, M. Lammerhofer, N.M. Maier, K. Rissanen, W. Lindner, Anal. Chem., 2002, 74, 5658.
  • [183] K. Kacprzak, N. Maier, W. Lindner, J. Chrom A., 2011, 1218, 1452.
  • [184] K. Kacprzak, N. Maier, W. Lindner, J. Sep. Sci., 2010, 33, 2590.
  • [185] K.M. Kacprzak, W. Lindner, J. Sep. Sci., 2011, 34, 2391.
  • [186] Ch.W. Hoffmann, R. Pell, M. Lammerhofer, W. Lindner, Anal. Chem., 2008, 80, 8780.
  • [187] G. Uccello-Barretta, F. Balzano, C. Quintavalli, P. Salvadori, J. Org. Chem., 2000, 65, 3596.
  • [188] G. Uccello-Barretta, S. Bardoni, F. Balzano, P. Salvadori, Tetrahedron: Asymmetry, 2001, 12, 2019.
  • [189] G. Uccello-Barretta, F. Mirabella, F. Balzano, P. Salvadori, Tetrahedron: Asymmetry, 2003, 14, 1511.
  • [190] G. Uccello-Barretta, F. Balzano, P. Salvadori, Chirality, 2005, 17 (Suppl.), S243.
  • [191] G. Uccello-Barretta, F. Balzano, S. Bardoni, L. Vanni, L. Giurato, S. Guccione, Tetrahedron Asymmetry, 2008, 19, 1084.
  • [192] K.-H. Kellner, A. Blasch, H. Chmiel, M. Lammerhofer, W. Lindner, Chirality, 1997, 9, 268.
  • [193] A. Maximini, H. Chmiel, H. Holdik, N.W. Maier, J. Membrane Sci., 2006, 276, 221.
  • [194] S.L. Wiskur, H. Ait-Haddou, J.J. Lavigne, E.V. Anslyn, Acc. Chem. Res., 2001, 34, 963.
  • [195] K. Kacprzak, J. Gawroński, Chem. Commun., 2003, 1532.
  • [196] K. Kacprzak, J. Grajewski, J. Gawroński, Tetrahedron: Asymmetry, 2006, 17, 1332.
  • [197] M. Jensen, H. Mehlhorn, Parasit. Res., 2009, 105, 609.
  • [198] N. Vale, R. Moreira, P. Gomes, Eur. J. Med. Chem., 2009, 44, 937.
  • [199] D.C. Warhurst, J.C. Craig, I.S. Adagu, D.J. Meyer, S.Y. Lee, Malaria J., 2003, 2, 26.
  • [200] B.S. Park, D.Y. Kim, P.J. Rosenthal, S.Ch. Huh, B.J. Lee, E.J. Park, S.M. Kim, J.E. Kim, M.H. Kim, T.L. Huh, Y.J. Choi, K.H. Suh, W.S. Choi, S.E. Lee, Bioorg. Med. Chem. Lett., 2002, 12, 1351.
  • [201] C. Bucher, C. Sparr, W.B. Schweizer, R. Gilmour, Chem. Eur. J., 2009, 15, 7637.
  • [202] D.J. Sullivan Jr, H. Matile, R.G. Ridley, D.E. Goldberg, J. Biol. Chem., 1998, 273, 31103.
  • [203] A. Dorn, R. Stoffel, H. Matile, A. Bubendorf, R.G. Ridley, Nature, 1995, 374, 269.
  • [204] J.J. Walsh, D. Coughlan, N. Heneghan, C. Gaynor, A. Bell, Bioorg. Med. Chem. Lett., 2007, 17, 3599.
  • [205] L.R. Klevans, R.J. Kelly, J.L. Kovacs, Arch. Int. Pharmacodynam. Ther., 1977, 227, 57.
  • [206] J. Sidorov, J. Am. Geriatric. Soc., 1993, 41, 498.
  • [207] S. El-Tawil, J. Evidence-Based Med., 2011, 4, 56.
  • [208] M. Man-Son-Hing, G. Wells, A. Lau, J. Gen. Intern. Med., 1998, 13, 600.
  • [209] E. Solary, D. Caillot, B. Chauffert, R.-O. Casasnovas, M. Dumas, M. Maynadie, H. Guy, J. Clin. Oncol., 1992, 10, 1730.
  • [210] T.P. Miller, E.M. Chase, R. Dorr, W.S. Dalton, K.S. Lam, S.E. Salmon, Anti-Cancer Drugs, 1998, 9, 135.
  • [211] C.W. Taylor, W.S. Dalton, K. Mosley, R.T. Dorr, S.E. Salmon, Breast Cancer Res. Treat., 1997, 42, 7.
  • [212] E. Solary, B. Drenou, L. Campos, P. De Cremoux, F. Mugneret, P. Moreau, B. Lioure, A. Falkenrodt, B. Witz, M. Bernard, M. Hunault-Berger, M. Delain, J. Fernandes, C. Mounier, F. Guilhot, F. Garnache, C. Berthou, F. Kara-Slimane, J.-L. Harousseau, Blood, 2003, 102, 1202.
  • [213] P. Genne, M.T. Dimanche-Boitrel, R.Y. Mauvernay, G. Gutierrez, O. Duchamp, J.-M. Petit, F. Martin, B. Chauffert, Cancer Res., 1992, 52, 2797.
  • [214] P. Genne, O. Duchamp, E. Solary, D. Pinard, J.P. Belon, M.T. Dimanche-Boitrel, B. Chauffert, Leukemia, 1994, 8, 160.
  • [215] E. Solary, L. Mannone, D. Moreau, D. Caillot, R.-O. Casasnovas, H. Guy, M. Grandjean, J.-E. Wolf, F. Andre, P. Fenaux, P. Canal, B. Chauffert, A. Wotawa, M. Bayssas, P. Genne, Leukemia, 2000, 14, 2085.
  • [216] A. Berkessel, B. Seelig, S. Schwengberg, J. Hescheler, A. Sachinidis, ChemBioChem, 2010, 11, 208.
  • [217] S.A. Nawaz, M. Ayaz, W. Brandt, L.A. Wessjohann, B. Westermann, Biochem. Biophys. Res. Commun., 2011, 404, 935.
  • [218] D.R. Reed, G. Zhu, P.A. Breslin, F.F. Duke, A.K. Henders, M.J. Campbell, G.W. Montgomery, S.E. Medland, N.G. Martin, M.J. Wright, Human Mol. Gen., 2010, 19, 4278.
  • [219] R.J. Aerts, W. Snoeijer, O. Aerts-Teerlink, E. van der Meijden, R. Verpoorte, Phytochem., 1991, 30, 3571.
  • [220] R.J. Aerts, W. Snoeijer, E. van der Meijden, R. Verpoorte, Phytochem., 1991, 30, 2947.
  • [221] R.J. Aerts, A. Stoker, M. Beishuizen, I. Jaarsma, M. Van De Heuvel, E. Van Der Meijden, R. Verpoorte, J. Chem. Ecol., 1992, 18, 1955.
  • [222] W.Z. Antkowiak, Wiad. Chem., 1998, 52, 474.
  • [223] J. Suszko, F. Szeląg, Bull. Int. Acad. Pol. Sci. Lett. Cl. Sci. Math. Nat., Ser. A, 1936, 403 (Chem. Abstr. 1937, 31, 1816).
  • [224] J. Gawroński, K. Gawrońska, J. Chem. Res., (S), 1984, 304.
  • [225] M. Brzostowska, J. Gawroński, Monatsh. Chem., 1984, 115, 1373.
  • [226] J. Gawroński, J. Koput, A. Wierzbicki, Z. Naturforsch., 1986, 41A, 1245.
  • [227] D.A. Lightner, J. Gawroński, W.M.D. Wijekoon, J. Am. Chem. Soc., 1987, 109, 6354.
  • [228] M. Brzostowska, Badania z zakresu asymetrycznej indukcji, Rozprawa doktorska UAM Poznań, 1988.
  • [229] J. Gawroński, M. Brzostowska, J. Koput, Croatica Chem. Acta, 1989, 62, 97.
  • [230] M. Kubicki, T. Borowiak, M. Gawron, M. Giel, J. Gawroński, J. Cryst. Spectr. Res., 1990, 20, 447.
  • [231] J. Gawroński, M. Brzostowska, D. Radocki, Pol. J. Chem., 1992, 66, 457.
  • [232] M. Kubicki, T. Borowiak, K. Gawrońska, J. Gawroński, Z. Naturfor. Sect. B, 2000, 55, 1083.
  • [233] J. Gawroński, K. Gawrońska, H. Wynberg, Chem. Commun., 1981, 307.
  • [234] J. Gawroński, K. Gawrońska, H. Kołbon, H. Wynberg, Recl. Trav. Chim. Pays-Bas, 1983, 102, 479.
Uwagi
PL
Błąd w numeracji biblografii - brak poz. 104.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-82b752f8-02bc-459b-a820-5da8de579ab1
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.