PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2014 | 12 | 10 | 1047-1055
Tytuł artykułu

Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A series of pyrimido[1,2-a]benzimidazole and α-cyanocinnamic acid derivatives have been synthesized in the reactions of Schiff bases 2–7 with selected nitriles containing an active methylene group: malononitrile 8–12, cyanoacetamide 13–16, benzyl cyanide 17–21, benzoylacetonitrile 22–24, cyanoacetate methyl ester 25–28 and benzylacetamide 29. The structures 8–29 were confirmed by the results of elementary analysis and their IR, 1H-, 13C-NMR and MS spectra. The products 8–29 of various chemical structure pyrimido[1,2-a] benzimidazole 8–12, 14–16, 17–21, 23–24, 26 and α-cyanocinnamic acid derivatives 13, 22, 25, 27, 28 were obtained, which are of interest for biological studies or which can be substrates for further synthesis. The selected compounds 10, 13, 14, 17, 19, 21, 23–25 and 28 were screened for their antiproliferative activity in vitro against neoplastic and normal cell lines. The most active two compounds were: 2-(o-bromophenylene)-3-cyano-4-phenyl-1,2-dihydropyrimido[1,2-a]benzimidazole (24) and 3-cyano-4-phenyl-2-(2,4-dimethoxyphenyl)-1,2-dihydropyrimido[1,2-a]benzimidazole (23). However, similarly like cisplatin used as the control, they showed no selectivity towards cancer cells, by inhibiting proliferation of normal mouse fibroblasts in similar manner.
Wydawca

Czasopismo
Rocznik
Tom
12
Numer
10
Strony
1047-1055
Opis fizyczny
Daty
wydano
2014-10-01
online
2014-05-15
Twórcy
autor
  • Wroclaw Medical University
  • Wroclaw Medical University
  • Polish Academy of Science
  • Polish Academy of Science
  • Wroclaw Medical University
Bibliografia
  • [1] The Merck Index, 14th edition (Whitehouse Station, USA, 2006)
  • [2] V.A. Anisimova, M.M. Osipova, A.A. Spasov, A.F. Turchaeva, G.P. Dudchenko, N.P. Larionov, S.G. Kovalcv, Pharm. Chem. J. 36, 468 (2002) http://dx.doi.org/10.1023/A:1021888520874[Crossref]
  • [3] A. Settimo, G. Primofiore, F. Settimo, A.M. Marini, Il Farmaco 47, 1293 (1992)
  • [4] J.P. Powers, S. Li, J.C. Jaen, J. Liu, N.P.C. Walker, Z. Wang, H. Wesche, Bioorg. Med. Chem. Lett. 16, 2842 (2006) http://dx.doi.org/10.1016/j.bmcl.2006.03.020[Crossref]
  • [5] P.F. Asobo, H. Wahe, J.T. Mbafor, A.E. Nkengfack, Z.T. Fomum, E.F. Sophue, D. Döpp, J. Chem. Soc. Perkin Trans. 1, 457 (2001) http://dx.doi.org/10.1039/b005511p[Crossref]
  • [6] J. Madden, J.R. Dod, R. Godemann, J. Kraemer, M. Smith, M. Biniszkiewicz, D.J. Hallett, J. Barker, J.D. Dyekjaer, T. Hesterkamp, Bioorg. Med. Chem. Lett. 20, 5329 (2010) http://dx.doi.org/10.1016/j.bmcl.2010.06.089[Crossref]
  • [7] P.P. Seth, E.A. Jefferson, L.M. Risen, S.A. Osgood, Bioorg.Med. Chem. 13, 1669 (2003) http://dx.doi.org/10.1016/S0960-894X(03)00245-2[Crossref]
  • [8] S.O. Podunavac-Kuzmanović, D.D. Cvetkovic, CI&CEQ 17, 9 (2011) http://dx.doi.org/10.2298/CICEQ100329044P[Crossref]
  • [9] T.A. Farghaly, N.A.A. Hafez, E.A. Ragab, H.M. Awad, M.M. Abdalla, Eur. J. Med. Chem. 45, 492 (2010) http://dx.doi.org/10.1016/j.ejmech.2009.10.033[Crossref]
  • [10] W.P. Nawrocka, Boll. Chim. Farm. 135, 18 (1996)
  • [11] W.P. Nawrocka, A. Nowicka, H. Liszkiewicz, Wiad. Chem. 66, 811 (2012) (in Polish)
  • [12] W.P. Nawrocka, A. Nowicka, H. Liszkiewicz, Wiad. Chem. 66, 839 (2012) (in Polish)
  • [13] W.P. Nawrocka, A. Nowicka, Wiad. Chem. 67, 715 (2013) (in Polish)
  • [14] A. Nowicka, W.P. Nawrocka, Wiad. Chem. 67, 695 (2013) (in Polish)
  • [15] A. Nowicka, W.P. Nawrocka, Wiad. Chem. 67, 203 (2013) (in Polish)
  • [16] W.P. Nawrocka, B. Sztuba, A. Dryś, J. Wietrzyk, J. Kosendiak, A. Opolski, Pol.J.Chem., 80, 279 (2006)
  • [17] W.P. Nawrocka, M.W. Kowalska, B. Sztuba, A. Dryś, J. Wietrzyk, B. Filip, Pol. J. Chem. 81, 1753 (2007)
  • [18] W.P. Nawrocka, B. Sztuba, M.W. Kowalska, H. Liszkiewicz, J. Wietrzyk, A. Nasulewicz, M. Pełczyńska, A. Opolski, Il Farmaco 59, 83 (2004) http://dx.doi.org/10.1016/j.farmac.2003.12.001[Crossref]
  • [19] M. Rai, S. Kumar, K. Krishan, A. Singh, Indian J. Chem. 17B, 287 (1979)
  • [20] M. Rai, K. Krishan, A. Singh, Indian J. Chem. 13, 991 (1975)
  • [21] F.A. Bassyouni, I.I. Ismail, Afinidad LVIII, 375, (2001)
  • [22] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision C.02 (Gaussian, Inc., Wallingford, CT, 2004)
  • [23] J. Wietrzyk, M. Chodynski, H. Fitak, E. Wojdat, A. Kutner, A. Opolski, Anticancer Drugs 18, 447 (2007) http://dx.doi.org/10.1097/CAD.0b013e3280143166[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-014-0533-3
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.