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2013 | 11 | 4 | 502-513
Tytuł artykułu

Synthesis, reactions and antineoplastic activity of 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromene derivatives

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Języki publikacji
EN
Abstrakty
EN
The key 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetates 3 were synthesized in high yields by cyclocondensation of 4-oxo-4H-chromen-3-carbaldehydes 1 with coumarin-3-acetic acids 2 under mild conditions. The reaction pathway involves aldol condensation and subsequent intramolecular lactonization to afford 2-oxo-2H,5H-pyrano[3,2-c]chromene skeleton 3. Further treatment of acetates 3 with alcohols, water or nitrogen containing compounds led to 5-alkoxy-, 5-hydroxy- or 5-acylamino-2H,5H-pyrano[3,2-c]chromen-2-ones 4-6 via nucleophilic substitution of acetyloxy group at C-5. Acetates and hydroxyl derivatives 3 and 5 undergo facile rearrangement in an acid medium yielding 5-hydroxypyrano[2,3-b]chromen-2(10aH)-ones 7. [...] Twelve prepared compounds were evaluated on their antineoplastic activities on 60 human tumour cell line panels in NCI USA. The obtained biological results confirmed that 3-(2-oxo-2H-chromen-3-yl)-2H,5H-pyrano[3,2-c]chromen-2-one represents a new leading skeleton suitable for further antitumour activity study.
Wydawca

Czasopismo
Rocznik
Tom
11
Numer
4
Strony
502-513
Opis fizyczny
Daty
wydano
2013-04-01
online
2013-01-23
Twórcy
  • Department of Chemistry, Faculty of Natural Sciences, University of Ss. Cyril and Methodius, 917 01, Trnava, Slovak Republic, gasparova@ucm.sk
autor
  • Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, 842 15, Bratislava, Slovak Republic
  • Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, 842 15, Bratislava, Slovak Republic
  • Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, 842 15, Bratislava, Slovak Republic
  • Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, 842 15, Bratislava, Slovak Republic
Bibliografia
  • [1] C.K. Ghosh, Heterocycles 63, 2875 (2004) http://dx.doi.org/10.3987/REV-04-586[Crossref]
  • [2] R. Gašparová, M. Lácová, Molecules 10, 937 (2005) http://dx.doi.org/10.3390/10080937[Crossref]
  • [3] D.H. Nam, K.Y. Lee, C.S. Moon, Y.S. Lee, Eur. J. Med. Chem. 45, 4288 (2010) http://dx.doi.org/10.1016/j.ejmech.2010.06.030[Crossref]
  • [4] T. Raj, R.K. Bhatia, R.K. Sharma, V. Gupta, D. Sharma, M.P.S. Ishar, Eur. J. Med. Chem. 44, 3209 (2009) http://dx.doi.org/10.1016/j.ejmech.2009.03.030[Crossref]
  • [5] J. Ungwitayatorn, C. Wiwat, W. Samee, P. Nunthanavanit, N. Phosrithong, J. Mol. Struct. 1001, 152 (2011) http://dx.doi.org/10.1016/j.molstruc.2011.06.035[Crossref]
  • [6] S. Lee, K. Sivakumar, W.-S. Shin, F. Xie, Q. Wang, Bioorg. Med. Chem. Lett. 16, 4596 (2006) http://dx.doi.org/10.1016/j.bmcl.2006.06.007[Crossref]
  • [7] N. Chen, N. Jain, J. Xu, M. Reuman, X. Li, R.K. Russell, Z. Sui, Tetrahedron Lett. 47, 5909 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.06.047[Crossref]
  • [8] C. N. Huang, P.Y. Kuo, C.H. Lin, D.Y. Yang, Tetrahedron, 63, 10025 (2007) http://dx.doi.org/10.1016/j.tet.2007.07.041[Crossref]
  • [9] J. Quiroga, A. Rengifo, B. Insuasty, R. Abonia, M. Nogueras, A. Sanchez, Tetrahedron Lett. 43, 9061 (2002) http://dx.doi.org/10.1016/S0040-4039(02)02316-X[Crossref]
  • [10] O. Fatunsin, V.O. Iaroshenko, S. Dudkin, S. Mkrtchyan, A. Villinger, P. Langer, Tetrahedron Lett. 51, 4693 (2010) http://dx.doi.org/10.1016/j.tetlet.2010.06.138[Crossref]
  • [11] M.A. Ibrahim, Tetrahedron, 65, 7687 (2009) http://dx.doi.org/10.1016/j.tet.2009.06.107[Crossref]
  • [12] M. Terzidis, C.A. Tsoleridis, J. Stephanidou-Stephanatou, Tetrahedron 63, 7828 (2007) http://dx.doi.org/10.1016/j.tet.2007.05.100[Crossref]
  • [13] J. Nawrot-Modranka, E. Nawrot, J. Graczyk, J. Eur. J. Med. Chem. 41, 1301 (2006) http://dx.doi.org/10.1016/j.ejmech.2006.06.004[Crossref]
  • [14] L.J. Legoabe, A. Petzer, J.P. Petzer Eur. J. Med. Chem. 49, 343 (2012) http://dx.doi.org/10.1016/j.ejmech.2012.01.037[Crossref]
  • [15] R. Gašparová, M. Lácová, A. Krutošíková, Collect. Czech. Chem. Commun. 70, 2101 (2005) http://dx.doi.org/10.1135/cccc20052101[Crossref]
  • [16] H. Stankovičová, A. Gáplovský, M. Lácová, J. Chovancová, A. Puchala, J. Heterocycl. Chem. 43, 843 (2006) http://dx.doi.org/10.1002/jhet.5570430405[Crossref]
  • [17] M. Lácová, R. Gašparová, P. Koiš, A. Boháč, H.M. El-Shaaer, Tetrahedron 66, 1410 (2010) http://dx.doi.org/10.1016/j.tet.2009.11.057[Crossref]
  • [18] M. Lácová, A. Boháč, Patent SK 287542 B6 (2011)
  • [19] A. Nohara, T. Umetani, Y. Sanno, Tetrahedron 30, 3553 (1974) http://dx.doi.org/10.1016/S0040-4020(01)97034-6[Crossref]
  • [20] S. Kováčová, L. Kováčiková, M. Lácová, A. Boháč, M. Sališová, Chem. Papers 64, 806 (2010) http://dx.doi.org/10.2478/s11696-010-0059-x[Crossref]
  • [21] C.K. Ghosh, C. Bandyopadhyay, Indian J. Chem., Sect. B 23, 1048 (1984)
  • [22] C.K. Ghosh, C. Bandyopadhyay, S. Biswas, A.K. Chandravarty, Indian J. Chem., Sect. B 29, 814 (1990)
  • [23] A.Y. Bochkov, V.N. Yarovenko, M.M. Krayushkin, T.A. Chibisova, T.M. Valova, V.A. Barachevskii, V.F. Traven, I.P. Beletskaya, Russian J. Org. Chem. 44, 595 (2008) http://dx.doi.org/10.1134/S1070428008040210[Crossref]
  • [24] L. Kováčiková, R. Gašparová, A. Boháč, M. Ďurana, M. Lácová, ARKIVOC 11, 188 (2010)
  • [25] M. Lácová, R. Gašparová, P. Koiš, A. Boháč, H.M. El-Shaaer, Tetrahedron 66,1410 (2010) http://dx.doi.org/10.1016/j.tet.2009.11.057[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0184-1
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