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Syntezy oliwacyny

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Warianty tytułu
EN
Synthesis of olivacine
Języki publikacji
PL
Abstrakty
EN
Olivacine (1,5-methyl-6H-pyrido[4,3-b]carbazole) is an isomer of ellipticine (5,11-dimethyl-6H-pyrido[4,3-b] carbazole). Both of these heterocyclic compounds are carbazole derivatives, which exhibit broad spectrum of biological activity [1], especially as antineoplastic agents [2–9]. These four-ring heterocycles can be isolated from natural sources [10–16], or prepared synthetically. Chemical literature described more than 20 method of synthesis of olivacine [2, 17–34]. In this paper we described five selected syntheses of this alkaloid. In the first one this compound can be obtained during a multistep synthesis starting from 1-benzenesulfonyl-2-lithioindole [35]. A shorter method to get olivacine was the condensation of indole with an ethylene ketal [35]. Third synthesis starts from obtaining benzenosulfonyloindol from indole [37]. Another way starts from the synthesis of 1-(tert-butoxy)carbonyloindol [38]. Fifth method to get olivacine is the synthesis from the 1H-indole -2-carboxylate [39].
Rocznik
Strony
983--995
Opis fizyczny
Bibliogr. 41 poz., schem.
Twórcy
autor
  • Katedra i Zakład Chemii Organicznej Uniwersytetu Medycznego we Wrocławiu ul. Borowska 211a, 50-556 Wrocław
autor
  • Katedra i Zakład Chemii Leków Uniwersytetu Medycznego we Wrocławiu ul. Borowska 211, 50-556 Wrocław
Bibliografia
  • [1] B.Ch. Nandy, A.K. Gupta, A. Mittal, V. Vyas, IJMASR, 2014, 1(1), 25.
  • [2] C.W. Mosher, O.P. Crews, E.M. Acton, L. Goodman, J. Med. Chem., 1966, 9, 237.
  • [3] H.P. Husso, R. Besselievre, P. Potier, J.B. Le pecq, C. Paolleti, Eur., Pat. Appl. EP, 1981, 42438.
  • [4] M. Maftouh, R. Besselievre, B. Monsarrat, P. Lesca, B. Meunier, P. Husson, C. Paoletti, J. Med. Chem. 1985, 20, 708.
  • [5] G.W. Gribble, The Alkaloids, A. Brossi (Red.), Academic Press, New York 1990, str. 239.
  • [6] K.L. Dalton, S. Demerac, B.C Elmes, J.W. Loder, M.J. Swan, T. Teitei, Aust. J. Chem., 1967, 20, 2715.
  • [7] C.N Garbett, D.C Graves, Curr. Med. Chem.- Anti.-Cancer Agents, 2004, 4, 149.
  • [8] M. Stiborová, J. Poljakowa, E. Martinkowá, L. Borek-Dohalská, T. Ecskchlager, R. Kizek, E. Frei, Interdiscip. Toxicol., 2011, 4(2), 98.
  • [9] L.K Dalton, S. Demerac, B.C. Elmes, J.W. Loder, J.M. Swan, T. Teitei, Aust. J. Chem., 1967, 20, 2715.
  • [10] J. Schmutz, F. Hunzicker, Pharm. Acta Helv., 1958, 33, 341.
  • [11] G.B. Marini-Bettolo, P. Carvalho-Ferreira, Rend. Ist Sup. Sanit., 1960, 23, 68.
  • [12] M.A. Ondetti, V. Deulofeu, Tetrahedron Lett., 1959, 7, 1.
  • [13] M.C Gorman, N. Neuss, N.J. Cone, J.A. Deyroup, J. Am. Chem. Soc., 1960, 82, 1142.
  • [14] S. Goodwin, A.F Smith, E.C. Horning, J. Am. Chem. Soc., 1959, 81, 1903.
  • [15] J.P. Cosson, M. Schmid, Phytochemistry, 1970, 9, 1353.
  • [16] C. Kan-Fan, B.C. Das, P. Potier, M. Schmid, Phytochemistry, 1970, 9, 1351.
  • [17] J. Schmutz, H. Wittwer, Helv. Chem. Acta, 1960, 43, 793.
  • [18] E. Wenkert, K.G. Dave, J. Am. Chem. Soc., 1962, 84, 94.
  • [19] R. Besselievre, H.P. Husson, Tetrahedron Lett., 1976, 22, 1873.
  • [20] J. Bergman, R. Carlsson, Tetrahedron Lett., 1978, 19, 24055.
  • [21] J.P. Kutney, M. Noda, N.G. Lewis, B. Monteiro, D. Mostowicz, B.R. Worth, Heterocycles, 1981, 16, 1469.
  • [22] T. Naito, N. Iida, I. Ninomiya, J. Chem. Soc. Chem. Com., 1981, 2, 44.
  • [23] Y. Murakami, Y. Yokoyama, N. Okuyama, Tetrahedron Lett., 1983, 24, 2189.
  • [24] Y. Murakami, Y. Yokoyama, N. Okuyama, Tetrahdron Lett., 1988, 24, 2189.
  • [25] I. Hogan, P.D. Jenkins, M. Sainsbury, Tetrahedron Lett., 1988, 29, 6505.
  • [26] I. Hogan, P.D. Jenkins, M. Sainsbury, Tetrahedron, 1990, 46, 2943.
  • [27] Y. Yokoyama, N. Okuyama, S. Iwadate, T. Momoi, Y. Murakami, J. Chem. Soc., Perkin Trans., 1990, 1, 1319.
  • [28] S. Hibino, E. Sugino, J. Heterocycl. Chem., 1990, 27, 1751.
  • [29] Y. Yokoyama, N. Okuyama, S. Iwadate, T. Momoi, Y. Murakami, J. Chem. Soc. Perkin Trans., 1990, 1, 1319.
  • [30] J.E. Bäckvall, N.A. Plobeck, J. Org. Chem., 1990, 55, 4528.
  • [31] R.J. Hall; J. Marchant; A.M.F. Oliveira-Campos, M.J.R.P. Queiroz, P.V.R. Shannon, J. Chem. Soc., Perkin Trans., 1992, 1, 3439.
  • [32] M. Ishikura, Y. Matsuzaki, I. Agata, N. Katagiri, Tetrahedron, 1998, 54, 13929.
  • [33] N.S. Narasimhan, M. Gokhale, J. Indian. Sci., 2001, 81, 135.
  • [34] Y. Miki, Y. Tsuzaki, H. Hibino, Y. Aoki, Synlett., 2004, 12, 2206.
  • [35] R. Besselievre, H.P. Husson, Tetrahedron, 1981, 37, (Suppl. 1), 241.
  • [36] A. Jackson, N.D.V. Wilson, A.J. Gaskell and J.A. Joule, J. Chem. Soc. C., 1969, 2738.
  • [37] J.P Kutney, M. Noda, N.G Lewis, B. Monteiro, D. Mostowicz, B. Wotrh, Can. J. Chem., 1982, 60, 2426.
  • [38] M. Ishikura, N. Takahashi, K. Yamada, T. Abe, R. Yanada, Helvetica Chimica Acta, 2008, 91, 1828.
  • [39] N. Ramkumar, R. Nagarajan, J. Org. Chem., 2014, 79, 736.
  • [40] G.B Marini-Bettolo, J. Schmurz, Helv. Chem. Acta, 1959, 42, 2146.
  • [41] M.A. Ondetti, V. Deulofeu, Tetrahedron, 1961, 15, 1-4, 160.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-e72217f3-a759-4e0e-96f4-c1087bf12d6f
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