Abstract
A series of 3-nitro-2-trifluoromethyl-2H-chromenes was synthesized by the reactions of salicylaldehyde derivatives with 3,3,3-trifluoro-1-nitroprop-1-ene. Further transformations of the synthesized chromenes gave hitherto unknown 3-amino-2-trifluoromethylchromanes promising as precursors for the synthesis of fused heterocyclic systems. Cytotoxicity assay first revealed the pronounced activity of several 2-nitro-2-trifluoromethyl-2H-chromenes against human tumor cell lines.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Pat. EA 015364; Byul. Izobret. [Invention Bull.], 2011, No. 3; http://www.eapo.org/ru/patents/reestr/.
G. P. Ellis, in The Chemistry of Heterocyclic Compounds, Ed. G. P. Ellis, Wiley, New York, 1977, p. 31.
D. Dauzonne, R. Royer, Eur. J. Med. Chem. Chim. Ther., 1984, 19, 477.
G. J. Finn, B. S. Creaven, D. A. Egan, Eur. J. Pharm. Sci., 2005, 26, 16.
R. Bergmann, R. Gericke, J. Med. Chem., 1990, 33, 492.
G. Burrell, F. Cassidy, J. M. Evans, D. Lightowler, G. J. Stemp, J. Med. Chem., 1990, 33, 3023.
S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320.
W. Dmovski, K. Piasecka-Maciejewska, Org. Prep. Proc. Int., 2002, 34, 514.
C.-L. Wang, H.-Q. Li, W.-D. Meng, F.-L. Qing, Bioorg. Med. Chem. Lett., 2005, 15, 4456.
M. Medebielle, R. Keirouz, E. Okada, D. Shibata, W. R. Dolbier, Tetrahedron Lett., 2008, 49, 589.
V. Yu. Korotaev, I. B. Kutyashev, V. Ya. Sosnovskikh, Heteroat. Chem., 2005, 16, 492.
V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, A. Yu. Barkov, E. G. Matochkina, M. I. Kodess, Tetrahedron, 2008, 64, 5055.
E. N. Stukan´, S. V. Makarenko, V. M. Berestovitskaya, Russ. J. Gen. Chem. (Engl. Transl.), 2011, 81, 155 [Zh. Obshch. Khim., 2011, 81, 157].
V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, M. I. Kodess, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 317 [Izv. Akad. Nauk, Ser. Khim., 2006, 309].
V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, M. I. Kodess, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 2020.[Izv. Akad. Nauk, Ser. Khim., 2006, 1945].
S. Iwata, Y. Ishiguro, M. Utsugi, K. Mitsuhashi, K. Tanaka, Bull. Chem. Soc. Jpn., 1993, 66, 2432.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday and to the 60th anniversary of A. N. Nesmeyanov Institute of Organo-element Compounds of the Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2551—2555, November, 2014.
Rights and permissions
About this article
Cite this article
Baryshnikova, M.A., Volkonskii, A.Y., Gusev, D.V. et al. 3-Nitro-2-trifluoromethyl-2H-chromenes and products of their reduction. Synthesis and cytotoxicity evaluation. Russ Chem Bull 63, 2551–2555 (2014). https://doi.org/10.1007/s11172-014-0775-4
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-014-0775-4