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Synthesis and Antiproliferative Activity in vitro of New 2-Aminobenzimidazole Derivatives. Part 2 [1]

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A series of 2-methylpyrimido[1,2-a]benzimidazole derivatives has been synthesized in the reactions of 2-aminobenzimidazole (1) with selected halogeno _-diketones: 1,1,1- trifluoro- 2, 1-chloro-1,1-difluoro- 3, 3-chloro-2,4-pentadione- 4 and with 4-fluorobenzoylacetone 5. 2-Aminobenzimidazole (1) in the reactions with _-chloro- and _- bromocinnamaldehyde gave Schiff bases 10 and 11 which have been subjected to reduction using NaBH4 and 3-benzylideno-1,2-dihydro- (12) and 3-benzylideno-1,2,9,10- tetrahydroimidazo[1,2-a]benzimidazole (13) were obtained. The structures 2-13 were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Compounds 2-13 were examined for their antiproliferative activity in vitro against the cells of 3 human cancer cell lines, using SRB (sulphorhodamine B) or MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) technique. Four out of all tested compounds revealed cytotoxic activity in vitro.
Rocznik
Strony
709--716
Opis fizyczny
Bibliogr. 31 poz., rys.
Twórcy
autor
  • Department of Technology of Drugs, Wrocław University of Medicine,50-140 Wrocław, Nankier Sq. 1, Poland
autor
  • Department of Physical Chemistry, Wroc³aw University of Medicine, 50-140 Wroc³aw, Nankier Sq. 1, Poland
  • Department of Technology of Drugs, Wrocław University of Medicine,50-140 Wrocław, Nankier Sq. 1, Poland
autor
  • Faculty of Chemistry, University of Wrocław, 50-383 Wrocław, Joliot-Curie Str. 14, Poland
autor
  • Department of Experimental Oncology, Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wrocław, R. Weigla Str. 12, Poland
autor
  • Department of Experimental Oncology, Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wrocław, R. Weigla Str. 12, Poland
autor
  • Department of Experimental Oncology, Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wrocław, R. Weigla Str. 12, Poland
Bibliografia
  • 1.Nawrocka W., Sztuba B., Kowalska W.M., Liszkiewicz H., Wietrzyk J., Nasulewicz A., Pelczynska M and Opolski A., Farmaco, 54, 83 (2004).
  • 2.Bastrop J.A., Richards C.G., Russel D.H. and Ryback G., J. Chem. Soc., 1132 (1959).
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  • 4.Staab H.A. and VOgtle R, Chem. Ber., 98, 2700 (1965).
  • 5.Mannschrcck A., Rissmann G., Vogtle R and Wild D., Chem. Ber., 100, 335 (1967).
  • 6.Nawojski A. and Nawrocka W,,Ann. Soc. Chim. Polonarum, 48, 1073 (1974).
  • 7.Liszkiewicz H., Kowalska M.W., Glowiak T., Wietrzyk J. and Opolski A., Polish J. Chem., 76, 160' (2002).
  • 8.Nawojski A., Prace Naukowe Akademii Medycznej we Wrodawiu, Akademia Medyczna, Wroclaw 5(10) (1969); (in Polish).
  • 9.Schmidt U. and Kubitzek H., Chem. Ber., 93, 1559 (1960).
  • 10.Joshi K.C. and Chand P., Heterocycles, 16, 43 (1981).
  • 11.Joshi K.C., Dubey K. and Dandia A., Heterocycles, 16, 1545 (1981).
  • 12.Joshi K.C. and Chand P., J. Heterocyclic Chem., 17, 1783 (1980).
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  • 15.Nawrocka W„ Polish J. Chem., 68, 2659 (1994).
  • 16.Nawrocka W., D.Sc. Thesis Wroclaw University of Medicine, Wroclaw 1999.
  • 17.Nawrocka W. and Zimecki M., Arch. Pharm. Pharm. Med. Chem., 331, 249 (1998).
  • 18.Nawrocka W., Zimecki M., Kuznicki T. and Kowalska MW., Arch. Pharm. Pharm. Med. Chem., 332, 85 (1999).
  • 19.Seth P.P., Jefferson E.A., Riesen L.M. and Osgood S.A., Bioorg. Med. Chem. Lett., 13, 1669 (2003).
  • 20.Asobo P.R, Wahe H., Mbafor J.T., Nkengfack A.E., Fomum Z.T., Sopbue E.F. and DiSpp D., Perkin Trans., 1,457 (2001).
  • 21.Niva T., Katagiri S. and Kato T., Jpn. Kokai Tokkyo Koho JP 61 63,680 [86 63,680] (1986); C.A. 105. 172498w (1986).
  • 22.Nikolova D., Ivanov R, Buyukliev S., Konstantinov M. and Karaivanova M., Arzneim.-Forsch. Drug Res., 51, 758 (2001).
  • 23.Gerger C.J., Agy in J.K. and Quada J.C. Jr.; U.S. US 6407131B1 18 Jun 2002; C.A. 137,3330 lz (2002).
  • 24.Gerger C.J., Agyin J.K. and Quada J.C. Jr.; U.S. USA6420411 B1 16 Jul 2002; C.A. 137,93753h (2002).
  • 25.Jia L., Wong H., Wang Y., Garza M. and Weitman S.D., J. Pharm. Sci., 91, 161 (2003).
  • 26.Rastogi R. and Sharma S., Synthesis, 861 (1983).
  • 27.Nawrocka., Bull. Chim. Farmaceutico, 135, 281 (1996).
  • 28.Mastalerz P., Chemia organiczna. Mechanizmy reakcji. 1970, WNT Warszawa, (in Polish).
  • 29.Nawrocka W., Liszkiewicz H., Opolski A. and Wietrzyk J., P 362880, 2003.
  • 30.Nawrocka W., Liszkiewicz H., Opolski A. and Wietrzyk J., P 362959, 2003.
  • 31.Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesh H., Kenney S. and Boyol M.R., J. Natl. Cancer. Inst., 82, 1107 (1990).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0080
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