Abstract
A number of chalcones with the (+)- and (−)-usnic acid moieties were synthesized by the following sequence: the reaction of these acids with phenylhydrazine, reduction of the C(1)=O group with sodium borohydride, O-methylation of the intermediate compounds with diazomethane, and subsequent condensation with substituted benzaldehydes at the acetyl group.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
D. Batovska, I. Todorova, Curr. Clin. Pharm., 2010, 5, 1.
S. Vogel, S. Ohmayer, G. Brunner, J. Heilmann, Bioorg. Med. Chem., 2008, 16, 4286.
O. Petrov, Y. Ivanova, M. Gerova, Catal. Commun., 2008, 9, 315.
K. Ingolfsdottir, Phytochemistry, 2002, 61, 729.
N. K. Honda, F. R. Pavan, R. G. Coelho, S. R. de Andrade Leite, A. C. Micheletti, T. I. B. Lopes, M. Y. Misutsu, A. Beatriz, R. L. Brum, C. Q. F. Leite, Phytomedicine, 2010, 17, 328.
H. Cetin, O. Tufan-Cetin, A. O. Turk, T. Tay, M. Candan, A. Yanikoglu, H. Sumbul, Parasitol. Res., 2008, 102, 1277.
K. Takahashi, M. Takani, Chem. Pharm. Bull., 1980, 28, 177.
E. Erba, D. Pocar, L. M. Rossi, Il Farmaco, 1998, 53, 718.
J. P. Kutney, I. H. Sanchez, Can. J. Chem., 1977, 55, 1079.
Protective Groups in Organic Chemistry, Ed. J. F. W. McOmie, Premium Press, 1973, 387 pp.
L. Bertilsson, C. Wachtmeister, Acta Chem. Scand., 1968, 22, 3081.
V. Galasso, Chem. Phys., 2010, 374, 138.
Yu. V. Tomilov, V. A. Dokichev, U. M. Dzhemilev, O. M. Nefedov, Usp. Khim., 1993, 62, 847 [Russ. Chem. Rev. (Engl. Transl.), 1993, 62].
D. N. Sokolov, O. A. Luzina, M. P. Polovinka, N. F. Salakhutdinov, Khim. Prirodn. Soedin., 2011, No. 2, 188 [Chem. Nat. Compd. (Engl. Transl.), 2011].
Pat. RF 2317076; Byul. Isobret. [Invention Bull.], 2008, No. 5.
M. Takai, Y. Uehara, J. A. Beisler, J. Med. Chem., 1979, 22, 1380.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2359–2364, November, 2011.
Rights and permissions
About this article
Cite this article
Sokolov, D.N., Luzina, O.A., Polovinka, M.P. et al. Synthesis of chalcones derived from (+)- and (−)-usnic acids. Russ Chem Bull 60, 2406–2411 (2011). https://doi.org/10.1007/s11172-011-0370-x
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-011-0370-x